Author: Jessica.F

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2396-83-0, name is Ethyl hex-3-enoate, A new synthetic method of this compound is introduced below., Safety of Ethyl hex-3-enoate

A solution of 2.32 mL (14.5 mmol) ethyl (E)-hex-3-enoate in 30 mL dry dichloromethane under nitrogen was cooled to -78 C and 23.0 mL (23.0 mmol) DIBAL (1 m in dichloromethane) was added over 45 min. After stirring for 1 h methanol (8 mL) was added carefully, followed 50 mL of an aqueous citric acid solution (10 %, m/V). After warming up to room temperature 20 mL brine was added and the organic layer separated. The aqueous layer was extracted with dichloromethane (3 x 30 mL) and the combined organic layers dried over sodium sulfate and evaporated carefully (600 mbar, bath temperature 40 C). The liquid residue was treated with 1.14 g (16.4 mmol) hydroxylamine hydrochloride and 6.0 mL (6.0 mmol) sodium hydroxide solution (6 m) under ice cooling. The mixture was stirred for 4 h at room temperature, then 2 mL glacial acetic acid and 100 mL water added, followed by extraction with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by FSC (dichloromethane) to give 0.865 g (7.64 mmol, 53%) of the oxime 3 as a 1:1 E/Z mixture as an unstable pale yellow oil.

The synthetic route of 2396-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lohrer, Bernhard; Bracher, Franz; Tetrahedron Letters; vol. 60; 51; (2019);,
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These common heterocyclic compound, 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: Methyl 2-methyl-2-phenylpropanoate

(b) Reaction of Methyl-alpha,alpha-dimethylphenyl acetic acid with 4-Chlorobutyryl chlorideMethyl-alpha,alpha-dimethylphenylacetic acid on Fridel-Craft’s acylation with 4-chlorobutyryl chloride in presence of anhydrous aluminum chloride in ethylene dichloride produced acylated Methyl-alpha,alpha-dimethylphenyl acetic acid, i.e., ketone intermediate as meta and para- isomers.More particularly, aluminum chloride was taken in dichloroethane and cooled in between about 0 to 2O0C. To the above pre cooled solution, Methyl-alpha,alpha-dimethylphenyl acetic acid was added at low temperature. To the reaction mixture, 4-chlorobutyryl chloride was added between about 0 to 20C. After addition of acid chloride the reaction mixture was stirred for about 8 to 10 hours at the same temperature. After completion of the reaction, mixture was quenched over chilled mixture of potable water and cone, hydrochloric acid followed by stirring the reaction mixture for another 4 hours. The reaction mixture was washed with aqueous solution of sodium bicarbonate and finally with water. Removal of dichloromethane provided Methyl-4-(4-chloro-l-oxobutyryl)-alpha,alpha-dimethylphenyl acetate (Ketone) in about 95 % HPLC purity.EXAMPLE 2Methyl-4-(4-chloro-l-oxobutyryl)- a, a-dimethyl phenyl acetate (Ketone)95 Kg (0.7124 Kmole) of aluminium chloride was taken in 120 Ltr dichloroethane and reaction mixture was cooled to 0 to 2O0C. To it was added ester of example 1, 46 Kg (0.2584 Kmole) through addition flask, maintaining the temperature 0 to 200C. Finally, to the reaction mixture was added 80 Kg (0.5673 Kmoles) of 4-chlorobutyryl chloride through addition flask maintaining the temperature 0 to 200C. After addition of acid chloride stirred the reaction mixture at 0 to 200C for 8 to 10 hours. After completion it was quenched over chilled mixture of potable water and concentrated hydrochloric acid. Then stirred the reaction mixture at 0 to 200C for 4 hours and finally extracted in dichloroethane. It was washed with 10% w/v aqueous solution of sodium bicarbonate and finally with water. Removal of the solvent under vacuum provides thick oily mass of Methyl-4-(4-chloro-l-oxobutyryl)-alpha-alpha-dimethyl phenyl acetate (Ketone). HPLC purity = 95%. Yield = 65 to 70 Kg.

The synthetic route of Methyl 2-methyl-2-phenylpropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WOCKHARDT LIMITED; JAWEED MUKARRAM, Siddiqui, Mohammed; MERWADE, Aravind, Yekanathsa; KHAN, Anjum, Reyaz; SOLANKI, Pawan, Vrajlal; WO2007/7347; (2007); A1;,
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Application of 1731-79-9, A common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, molecular formula is C14H26O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 4 [00088] The following Example describes the transesterification of dimethyl dodecanedioate using p-toluenesulfonic acid catalyst and the preparation of DDDA diester using a mixture of 50 mole % Exxal 13 and 50 mole % 1H, 1H, 5H-octafluoro-1-pentanol. [00089] A mixture of 51.68 g dimethyl dodecanedioate (0.2 mole), 41.58 g Exxal 13 (0.21 mole), 48.73 g 1H, 1H, 5H-octafluoro-1-pentanol (0.21 mole), and 0.38 g p-toluenesulfonic acid was heated, and methanol distilled off. When the reaction temperature reached 198 C., GC analysis showed the dimethyl dodecanedioate to be essentially gone, indicating that the reaction had gone nearly to completion. After cooling, the product was washed with brine, 1% aqueous NaOH, and water, then treated with basic alumina and filtered. The final acid number was 0.1 mg KOH/g. [00090] The same basic procedure was used to prepare other diesters, listed in Table 6. The non-fluorinated alcohol was Exxal 13 in all cases.[TABLE-US-00007] TABLE 6 DDDA diesters prepared according to Example 4. Mole fractionAcid PartiallypartiallynumberWt % FWt % FPrepara-Fluorinatedfluorinated(mg(elemental(bytionalcoholalcoholKOH/g)analysis)NMR) 30Telomer0.025 1.121.24 alcohol-L311H, 1H, 5H-0.50.1 octafluoro-1- pentanol321H, 1H, 2H,0.50.1 2H-perfluoro- 1-octanol331H, 1H0.50.1 heptafluoro- 1-butanol341H, 1H-0.50.1 perfluoro-1- octanol35Telomer0.0252 alcohol36Telomer0.0250.521.451.63 alcohol

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; E. I. du Pont de Nemours and Company; US6734320; (2004); B2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 191478-99-6, name is Methyl 4-amino-2,6-difluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 191478-99-6

4-(Chlorosulfonyl)benzoic acid (25.0 g, 113 mmol) and methyl 4-amino-2,6-difluorobenzoate (19.0 g, 101 mmol) were dissolved in methylene chloride (500 ml), and pyridine (25.0 ml, 285 mmol) was added thereto, followed by stirring at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure. The obtained residue was diluted with water, and then the pH was adjusted to 1.0 by adding 6 N hydrochloric acid. The precipitated solid was filtered, and washed with water. The obtained solid was resuspended in water, and washed with a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate (100 ml×2). The pH of the obtained aqueous layer was adjusted to 6.0 by adding 6 N hydrochloric acid thereto, followed by extraction with ethyl acetate (100 ml×2). The extraction liquids were combined, washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed to obtain the title compound (15.0 g, 36%). [0213] 1H NMR (d-DMSO, 400 MHz): delta 11.50 (s, 1H), 8.14 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 6.67 (d, J=10.4 Hz, 2H), 3.87 (s, 3H); MS (ESI) m/z 372 (M+H)+

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18830-44-9, name is Methyl 3,3,3-trifluoropropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H5F3O2

Put 67.1g of sodium hydroxide and 300g of deionized water into a 500ml reaction bottle, cool the ice water bath to 5 10 , drop 216.6g of methyl trifluoropropionate above, control the internal temperature below 30 , and continue stirring after the dripping 30min.Concentrated hydrochloric acid was added dropwise to the reaction bottle until the pH of the reaction solution was below 2, and stirring was continued for 30 min after completion of the drop.300 g of dichloromethane was added to the reaction flask for extraction twice, and the dichloromethane was concentrated and recovered to obtain crude trifluoropropionic acid.Set up a vacuum distillation device, vacuum distillate crude trifluoropropionic acid, collect 83 ~ 85 fraction (vacuum degree -0.097MPa), which is 3,3,3-trifluoropropionic acid, weight 199g, purity 99.2%, yield 88.0%, total reaction yield 66.2%.

The synthetic route of 18830-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan Youse Chenzhoufu Chemical Co., Ltd.; Wang Gang; Peng Zhimin; Li Zhipeng; Yin Demei; Zhang Zhenhua; (8 pag.)CN110903183; (2020); A;,
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Application of 331779-03-4, These common heterocyclic compound, 331779-03-4, name is Ethyl 2-(4-bromophenyl)acrylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of ester (20 mmol, 1.0 equiv) in toluene (40 mL) was addedparaformaldehyde (1.80 g, 60 mmol, 3.0 equiv), K2CO3 (8.29 g, 60 mmol, 3.0 equiv),n-Bu4NI (370.0 mg, 1.0 mmol, 0.05 equiv). The reaction mixture was heated to 60 Covernight. After the finish of reaction monitored by TLC, the reaction was cooled toroom temperature, water was added and the aqueous layer was extracted with Et2O(40 mL × 3). The combined organic layer was dried over anhydrous Na2SO4,concentrated in vacuo. The resulting residue was purified by column chromatographyto give the corresponding acrylate intermediate as a colorless oil. Then, a solution ofsubstituted amine (20 mmol, 2.0 equiv)in THF (13.0 mL) at 0C was added a solutionof corresponding acrylate (10 mmol, 1.0 equiv) in THF (7.0 mL) via addition funnel.The reaction mixture was allowed to warm to ambient temperature then stirred atroom temperature for 24h, and concentrated under vacuum. The resulting residue waspurified by column chromatography to give the corresponding intermediate as a oil.Then to a solution of the oil in dichloromethane (20.0 mL) were added di-tert-butyldicarbonate (2.40 g, 11 mmol) and DMAP (122.0 mg, 1 mmol), and the mixture wasstirred at room temperature for 24h. Saturated aq. NH4Cl was added to the mixtureand the resulting mixture was extracted with dichloromethane. The combined organiclayer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo.The resulting residue was purified by column chromatography to give thecorresponding intermediate as a colorless oil. Then to a solution of the resulting oil inTHF/H2O (5 mL/5 mL) was added LiOH (1.20 g, 50 mmol, 5 equiv). The reactionmixture was heated at 60 C overnight. After cooling to room temperature, thereaction was acidified using aqueous HCl (6 M), and the aqueous layer was extractedwith Et2O (20 mL × 3). The combined organic layer was washed with water and brine,dried over Na2SO4, and concentrated in vacuo to give the resulting product 4a-j as acolorless crystal, using for the next step without further purification.

The synthetic route of 331779-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Li; He, Gu; Pan, Zhaoping; Wu, Fengbo; Yu, Meng; Zeng, Minghui; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Related Products of 1462-12-0, A common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, molecular formula is C9H14O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Isatin Schiff base 2 (22.2 mg, 0.1 mmol), the corresponding electrophile (0.2 mmol), and catalyst I (6.0 mg, 0.01 mmol) were stirred in toluene or 1,2-DCE (0.3 mL) at the reported temperature for the appropriate time (Tables 2 and 3). In the case of the reactions carried out at 2 or -25 C, the reaction vessel containing the reagents and the solvent were cooled prior to mixing together. The reactions were followed by TLC (CH2Cl2-EtOAc, 20:1). The hydrolysis was carried out in situ by adding a mixture of THF and 10% aq HCl (3:1, 1 mL) with vigorous stirring for 15-20 min. The reaction mixture was transferred to separatory funnel, diluted with H2O (10 mL), and extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4), concentrated, and the product was isolated by column chromatography. The racemic standards were obtained by the same procedure using 1 equiv of K2CO3 as catalyst. After the completion of the reaction, the mixture was separated from K2CO3, hydrolyzed, and purified in the same manner.

The synthetic route of 1462-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?ari, Sergei; Metsala, Andrus; Kudrjashova, Marina; Kaabel, Sandra; Jaerving, Ivar; Kanger, Tonis; Synthesis; vol. 47; 6; (2015); p. 875 – 886;,
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Application of 40640-98-0, The chemical industry reduces the impact on the environment during synthesis 40640-98-0, name is Ethyl 3-(4-bromophenyl)propanoate, I believe this compound will play a more active role in future production and life.

A mixture of a 60% suspension of sodium hydride in mineral oil (4.8 g, 120 mmol) in N, N-dimethylformamide (50 mL) at about 5 C was treated with diethyl malonate (36.4 mL, 240 mmol). The mixture was stirred for about 5 minutes, slowly treated with a solution of 4- bromobenzyl bromide (20.0 g, 80 mmol) in N, N-dimethylformamide (20 mL), stirred at room temperature overnight, diluted with water, and extracted with ethyl acetate. The combined organic extracts were dried (MgS04), filtered, and concentrated under high vacuum. The residue was dissolved in a mixture of acetic acid (46 mL), water (30 mL), and concentrated sulfuric acid (13 mL) and was heated to reflux for 18 hours. The reaction mixture was cooled, concentrated under high vacuum, and diluted with water. The formed crystalline solid was collected by filtration, washed with water and diethyl ether, and was dried under high vacuum to provide the desired product. MS (DCI-NH3) : m/z 246,248 (M+NH4) +.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 3-(4-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; MAKOTO, Aoyama; WO2005/95387; (2005); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)acetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-(2,4-Dimethoxyphenyl)acetate

General procedure: To a stirred solution of acid 9 (320 mg, 1.76 mmol) in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed under vacuum. The crude product acid chloride was directly used for the next reaction without further purification. A solution of compound 1114 (554 mg, 2.64 mmol) in THF (6 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.44 mL, 3.52 mmol) and i-Pr2NH (0.49 mL, 3.52 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 12 (500 mg, 76%) as yellowish oily compound.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Synthetic Route of 6065-54-9, These common heterocyclic compound, 6065-54-9, name is Dimethyl 2,2-dimethylmalonate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: 2.63 g Mg in 75 ml anhydrous THF are preheated to 55C, treated with 20 mg iodine and 20 mg methyl iodide, 25.7 g of 5-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran (see below) are added maintaining reflux of the reaction, and the reaction is heated to reflux for 3 h until most of the Mg disappeared. 20 g dimethyl dimethylmalonate are solved in 40 ml anhydrous THF, cooled to – 6OC, and the freshly prepared Grignard reagent is added drop wise over 1 h at this temperature. The reaction is allowed to warm to 5C and quenched with 250 ml saturated aqueous ammonium chloride solution. The reaction is extracted with ether twice, the combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The crude product may contain some unreacted dimethyl dimethylmalonate, which could largely be distilled off under vacuum. The crude product is used for the cyclisation reaction without further purification.;

Statistics shows that Dimethyl 2,2-dimethylmalonate is playing an increasingly important role. we look forward to future research findings about 6065-54-9.

Reference:
Patent; NYCOMED GMBH; SCHLEMMINGER, Imre; SCHMIDT, Beate; FLOCKERZI, Dieter; TENOR, Hermann; ZITT, Christof; HATZELMANN, Armin; MARX, Degenhard; BRAUN, Clemens; KUeLZER, Raimund; HEUSER, Anke; KLEY, Hans-Peter; STERK, Geert Jan; WO2010/55083; (2010); A1;,
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