Tag: M.W=200-300

Reference of 6836-21-1, 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. 6836-21-1, name is Ethyl 2-(7-methoxynaphthalen-1-yl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(2-methoxy naphthalen-8-yl)acetate (2.0 g, 8.1 mmol)was dissolved in ethanol (40 mL, 20 vol) and cooled to -78 to-74 C, ammonia gas was purged to reaction mass for 30 minat -78 to -74 C, after purging slowly allowed to 25-30 C and stir for 2 h. The reaction mass stored for 48 h at 25-30 C,then mass was concentrated completely under reduced pressureto obtained crude material which was triturated in toluene (20mL, 10 vol) for 1 h and filtered the solid, then washed withtoluene (10 mL, 5 vol) suck dried the compound to get paleyellow coloured solid (1. 5 g, 87.6 % yield).IR (KBr, numax, cm-1): 3395, 3203, 2939, 2831, 1643, 1401,1259, 1203, 1024, 827 ; 1H NMR (400 MHz, DMSO-d6): delta7.84 (d, J = 8.8 Hz, 1H), 7.73 (d, J = 7.0 Hz, 1H), 7.61 (brs,1H), 7.4 (t, J = 6.8 Hz, 2H), 7.28 (t, J = 7.2 Hz, 1H), 7.19 (dd,J1 = 2.0 Hz, J2 = 9.2 Hz, 1H), 7.02 (brs, 1H), 3.87 (s, 3H), 3.81(s, 2H); 13C NMR (100Hz, DMSO-d6): delta 172.14, 157.22,133.14, 131.67, 129.87, 128.65, 128.20, 126.62, 123.01,117.58, 103.37, 55.11; EI-MS m/z (%): 216 (M + 1, 84), 199(27), 171 (100).

The synthetic route of Ethyl 2-(7-methoxynaphthalen-1-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gurunadham; Raju, R. Madhusudhan; Venkateswarlu; Asian Journal of Chemistry; vol. 28; 6; (2016); p. 1367 – 1370;,
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583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: esters-buliding-blocks

General procedure: To a solution of 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl iodide (0.22 mL, 1.0 mmol), ethyl benzoate (0.16 mL, 1.1 mmol) in Et2O (3 mL) was added at -80C methyllithium (1.5 M in Et2O with lithium bromide; 0.73 mL, 1.1 mmol) and stirring was continued for 30 min at the same temperature where diethyl-aluminium chloride (1 M in n-hexane; 1.1 mL, 1.1 mmol) was gradually added and further stirring for 15 min at -80 C. In a separate flask, lithium bromide (0.12 g, 1.4 mmol), triethyl phosphonoacetate (0.26 mL, 1.3 mmol), and THF (1 mL) was mixed at 0 C where triethylamine (0.19 mL, 1.4 mmol) was added and the solution was stirred for 10 min at room temperature. This mixture was slowly introduced to an aluminium acetal solution prepared above with the aid of cannula and the whole mixture was further stirred for 1 h at room temperature. To this solution were successively added Et2O (3 mL), NaF (0.185 g, 4.4 mmol) and H2O (59 mg, 3.3 mmol), which was stirred for 0.5 h at room temperature. Filtration with a pad of silica gel and concentration furnished a crude mixture which was purified by silica gel column chromatography (n-hexane:CH2Cl2=6:1) to afford 0.484 g (0.979 mmol, 98% yield, E_Z=>99:1) of the title compound 5ca as a colourless oil.

The synthetic route of 583-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamazaki, Takashi; Mano, Noriko; Hikage, Reo; Kaneko, Tsutomu; Kawasaki-Takasuka, Tomoko; Yamada, Shigeyuki; Tetrahedron; vol. 71; 42; (2015); p. 8059 – 8066;,
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3549-23-3, name is Methyl 2-(4-(tert-butyl)phenyl)acetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: Methyl 2-(4-(tert-butyl)phenyl)acetate

The appropriate aryl-ester 18a-e (1 eq), was added of EtOH (2.22 ml*mmol/eq) followed by hydrazine monohydrate (3 eq). The solution was refluxed overnight, then cooled to room temperature. The precipitate obtained was filtered and washed with cold EtOH and n-hexane to give the pure product. Synthesised as described above for hydrazides 19a-e. Obtained as a yellow oil in 88percent yield as a white solid.1H-NMR (DMSO-d6), delta: 1.26 (s, 9H), 3.30 (s, 2H), 4.13 (bs, 2H), 7.18 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 8.2 Hz, 2H), 9.18 (bs, 1H). 13C-NMR (DMSO-d6): delta: 31.1, 39.9, 34.1, 124.7, 124.8, 133.2, 148.6, 169.6.

The synthetic route of 3549-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 56 – 68;,
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2905-69-3, name is Methyl 2,5-dichlorobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2905-69-3

Add 19.1 g of 2,5-dichlorobenzoic acid (0.1 mol) and 120 ml of methanol to the reaction flask.Add a catalytic amount of acid and reflux at 65~70 C for 8 hours.After the reaction, the excess methanol was distilled off under reduced pressure.19.2 g of methyl 2,5-dichlorobenzoate was obtained in a yield of 93.6%.The obtained methyl 2,5-dichlorobenzoate (0.094 mol) was added to the reaction flask.Add 30 g of bromine (0.19 mol) and 2.5 g of aluminum tribromide.The reaction was carried out at 50 C for 6 hours, and after the reaction was completed, it was extracted with ethyl acetate and water.After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 24 g of Compound 3.The yield was 90.2%.Adding the obtained compound 3 to the reaction flask,Add 60 ml of methanol and a suitable palladium catalyst and react at 80 C for 6 hours.The reaction was extracted, dried, and the solvent was evaporated under reduced pressure to give 17.1 g of Compound 4.The yield was 86%.Finally, the compound 4 was placed in a reaction flask, 100 ml of deionized water was added, and an appropriate amount of acid was added, and the reaction was carried out at 60 C for 3 hours. After the reaction was completed, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The final product, dicamba, 14.5 g was obtained after pressure distillation.The total yield is 65%.

The synthetic route of 2905-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Yu Guoquan; Sun Xialin; Ma Changqing; Ding Huaping; (6 pag.)CN109134232; (2019); A;,
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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. 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H7Cl2NO2

(i) Sodium nitrite (20 g) in water (50 ml) was added to a stirred mixture of methyl 4-amino-3,5-dichlorobenzoate (6.23 g) in concentrated sulphuric acid (110 g) and water (95 ml) at 0C. The mixture was stirred until all the solid had dissolved (overnight at 0C). To the stirred solution was added a solution of potassium iodide (25 g) in water at 50C and the resulting mixture was stirred at 20C overnight. The mixture was extracted with diethyl ether. The ethereal extracts were washed with aqueous sodium bisulphite solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was chromatographed on silica, eluding with hexane: dichloromethane 7:3. 3.75 g of methyl 3,5-dichloro-4-iodobenzoate was obtained. Nuclear magnetic resonance spectrum (NMR) was as follows: ‘H (ppm from TMS in CDCl3, integral, number of peaks): 3.90, 3H, s; 7.95, 2H, s. Mass spectrum M+1 331.

The synthetic route of 41727-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE WELLCOME FOUNDATION LIMITED; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; EP279698; (1990); A3;,
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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. 1731-79-9, name is Dimethyl dodecanedioate, A new synthetic method of this compound is introduced below., SDS of cas: 1731-79-9

1,12-dodecanedioic acid dimethyl ester (1000.0g, 3.87 mols) was put into a reactor, heated and stirred under a reduced pressure of 80kPa at 105C. Methanol was distilled off while the mixture of gamma-butyrolactone (83.3g, 0.97 mol) and 28% by weight of sodium methoxide solution in methanol (186.7g, 0.97 mols) prepared at the room temperature was dropped into the heated 1,12-dodecanedioic acid dimethyl ester in 30 minutes. After continuing the reaction for 30 minutes then, the pressure was reduced to 26.7 kPa to further continue the reaction for 240 minutes. Next, after returning to ordinary pressure, the reactant was cooled to 70C and, while being stirred, methyliodide (137.7g, 101.6 mols) was dropped into it in 30 minutes. N-hexane (700g) and, next, water (3009) were poured into it. After removing the water layer, it was washed with aqueous solution of 10% sodium hydroxide (150g: twice) and water (200.0g: twice). N-hexane was distilled off under a reduced pressure. The remained oily substance was subjected to a distillation under a reduced pressure (oil bath temperature 200C/60 to 130Pa) and excessive 1,12-dodecanedioic acid dimethyl ester was distilled off. 762.9g of a distilled substance and 264.2g of a distillation residue were obtained. As a result of an analysis of the distillation residue by gas chromatography, it was found that 80.7% by weight of the compound indicated by the general formula (2) (n = 10, R = Me) was contained. This was mixed with aqueous solution of 10% sodium hydroxide (675g) and heated/refluxed for 5.5 hours. After diethylene glycol (230g) and 60% hydrazine monohydrate (124g) were added to the reaction liquid and stirred for one hour at 110C, the temperature of the reaction system was elevated to 170 to 200C while removing water, and after aqueous solution of 30% sodium hydroxide (100g) was dropped into it in 4 hours, it was stirred for 6 hours at that temperature. While pouring water (930g) into it, it was cooled, and with addition of diluted sulfuric acid it was extracted with toluene. After the organic layer was washed with water, the solvent was removed under a reduced pressure, and 254g of a crystalline residue containing 13-methyl-15-hydroxypentadecanoic acid (n = 10) as the main component was obtained. This was cyclized by intramolecular ester interchange reaction to thereby obtain 80.7g of a cyclic compound. This contained 98.9% by weight of 13-methyl-15-pentadecanolide. The yield was 32 mol%/butyrolactone. 1H-NMR(CDCl3,400MHz) 4.16(2H)m; 2.32(2H)m; 0.90(3H)d J=6.4Hz 13C-NMR(CDCl3) 173.89; 61.86; 35.31; 34.49; 34.20; 30.82; 27.68; 27.25; 26.57; 26.42; 26.26; 26.10; 25.87; 24.89; 24.52; 19.51 IR(film) 2930; 2860; 1740; 1460; 1350; 1245; 1173; 1115 MS 254(5); 236(9); 225(11); 207(21); 111(16); 97(35); 83(42); 70(100); 55(68); 41 (40)

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; SODA AROMATIC COMPANY, LIMITED; EP1741706; (2007); A1;,
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Electric Literature of 139911-28-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 2a. 8-fluorophenanthridin-6-ol.A mixture of methyl 2-bromo-5-fluorobenzoate (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80 C for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-5-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; ABBOTT LABORATORIES; MCDANIEL, Keith, F.; CHEN, Hui-ju; SHANLEY, Jason, P.; GRAMPOVNIK, David, J.; GREEN, Brian; MIDDLETON, Timothy; HOPKINS, Todd; OR, Yat, Sun; WO2012/92411; (2012); A2;,
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Electric Literature of 142-91-6, 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. 142-91-6, name is Isopropyl palmitate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.41 g of isopropyl palmitate (manufactured by Wako Pure Chemical Industries Ltd.), 1.00 g of phytosphingosine,and 14 mL of ethanol were added in a 30-mL eggplant flask and the mixture was stirred in a 55C hot water bath for 15min. After it was confirmed that the reaction system was homogeneous, 17.7 mg of potassium hydroxide (manufacturedby Kanto Chemical Co. , Inc.) was added. After 2 hours, a precipitate was confirmed and the mixture was continuouslystirred during a whole day and night. After the resulting reaction mixture was cooled to 30C, the precipitate was filteredand washed to obtain 1.45 g of N-hexadecanoyl-phytosphingosine in the form of a white solid in a yield of 82.9% (purity:95%).Melting point 114-117CIR (ATR, cm-1) 3336, 2917, 2849, 1611, 1542, 1468, 1076, 717MS (positive): [M + H]+ = 556.7, [M + Na]+ = 584.71H-NMR (deuterated pyridine, 500MHz, delta) 0.85 (3H, t, J = 7.0Hz), 0.85 (3H, t, J = 7.0Hz), 1.16-1.49 (46H, br), 1.69 (1H,m), 1.82 (2H, m), 1.94(2H, m), 2.24 (1H, m), 2.45 (2H, t, J = 7.6Hz), 4.29 (1H, m), 4.40 (1H, ddd, J = 5.9, 5.9, 5.5Hz),4.49 (2H, m), 5.10 (1H, m), 6.19 (1H, d, J = 6.7Hz), 6.53 (1H, d, J=6.2Hz), 6.62 (1H, t, J=5.4Hz), 8.52 (1H, d, J=8.5Hz)

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, Isopropyl palmitate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kao Corporation; HASHIMOTO, Hiroshi; SUGAI, Yoshiya; EP2757090; (2014); A1;,
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Reference of 6091-64-1, These common heterocyclic compound, 6091-64-1, name is Ethyl 2-bromobenzoate, 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.

To a tube was added Hphosphinate 3a (173 mg, 1 mmol, 1 equiv), Pd(OAc)2 (4.5 mg, 0.02 mmol, 2 mol %), xantphos (12.7 mg, 0.022 mmol, 2.2 mol %), toluene and 1,2-dimethoxyethane (4.5 ml : 0.5 ml), i-Pr2NEt (0.23 ml, 1.3 mmol, 1.3 equiv) and ethyl-2-bromobenzoate (0.24 mL, 1.5 mmol, 1.5 equiv). The homogeneous mixture was stirred under a flow of N2 for 10 minutes and then heated at 115C for 24 hrs. The solvent was then evaporated and the resulting residue partitioned between EtOAc (10 ml) and NaHCO3 (5 ml). The aqueous layer was extracted with EtOAc (3x). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The resulting oil was then purified by chromatography (silica gel, hexane/ EtOAc, 5:5) to give a yellow oil. Yield: 83% (232 mg); 1H NMR (CDCl3, 300 MHz) delta 8.04-8.11 (m, 1H), 7-77-7.81 (m, 1H), 7.59-7.64 (m, 2H), 4.41 (q, J = 7.0 Hz, 2H), 3.75-4.07 (dm, 2H), 1.90 (d, J = 15.2 Hz, 3H), 1.60-1.67 (m, 2H), 1.35-1.47 (m, 5H), 0.92 (t, J = 7.3 Hz, 3H) ppm; 13C NMR (CDCl3, 75.45 MHz) delta 168.1 (d, JPCCC = 3.4 Hz), 135.9 (d, JPCCC = 7.8 Hz), 133.9 (d, JPCCC = 8.1 Hz), 132.0 (d, JPCCCC = 2.3 Hz), 131.6 (d, JPC = 120.6 Hz), 131.0 (d, JPCC = 11.5 Hz), 129.7 (d, JPCC = 9.8 Hz), 64.5 (d, JPOC = 6.3 Hz), 61.9, 32.6 (d, JPOCC = 6.6 Hz), 18.9, 17.3 (d, JPC = 103.9 Hz), 14.2, 13.7 ppm; 31P NMR (CDCl3, 121.47 MHz) delta 43.07 ppm; HRMS (EI+) calcd for C14H21O4P 284.1177, found 284.1179.

Statistics shows that Ethyl 2-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 6091-64-1.

Reference:
Article; Gavara, Laurent; Petit, Christelle; Montchamp, Jean-Luc; Tetrahedron Letters; vol. 53; 37; (2012); p. 5000 – 5003;,
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Synthetic Route of 206551-41-9, These common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, 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 198 3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester To 0.096g (0.5 mmol) of 4-methoxyphenylsulphonamide in 3mL of DMF was added in one portion 0.020g (0.50 mmol) of 60percent sodium hydride and the reaction was stirred at 25-C for 15 min. Then, 0.135g (0.58 mmol) of methyl 3-bromo-2-fluorobenzylate was added to the solution in one portion and the resulting mixture was heated at 90 ¡ãC (bath temperature) for 18h. The reaction was cooled to room temperature, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica eluding with 30percent-50percent ethyl acetate/hexane to provide 0.037g (19percent) of the desired product. 1H-NMR(CDCl3): 8 ppm (s, 1H, NH), 6.8-7.8 ppm (m, 7H, Ar), 3.9 ppm (s, 1H, OMe), 3.7 ppm (s, 1H, OMe).

The synthetic route of 206551-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
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