Month: May 2021

Synthetic Route of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 1: A solution of n-butyl lithium in hexane (1.4M, 45.75 mL, 0.07 mol) was added drop wise to a solution of freshly distilled diisopropylamine (10.2 mL, 0.06 mol) in dry THF (200 mL) at -60 C. under nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (9.48 g, 0.06 mol) added drop wise over a period 30 min. Reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) reaction mixture was added drop wise 1,10-dibromodecane (20.0 g, 0.06 mol) in dry THF (20 mL) and DMPU (1.79 g, 0.01 mol). Then the temperature was allowed to reach room temperature and stirred at same temperature over a period of 16 h The resulting reaction mixture was quenched with saturated NH4Cl (500 mL) at 0 C. and the reaction mixture was extracted with ethyl acetate (300 mL¡Á3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (0.5% ethyl acetate in petroleum ether) to give product as colorless oil 8.0 g (33%).1H NMR (300 MHz, DMSO-d6) delta (ppm): 0.62-0.64 (m, 2H), 0.94-0.98 (m, 2H), 1.25 (bs, 12H), 1.37 (s, 9H), 1.39-1.43 (m, 4H), 1.73-1.80 (m, 2H), 3.52 (t, J=6.6 Hz, 2H).

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; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
Ester – Wikipedia,
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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. 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8Br2O4

Example 11Production of Compound 15 A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(10.6 g, 30.0 mmol) synthesized according to the method of a literature (Macromolecules, 1999, 32, 2455), Compound 15 (made by Sigma-Aldrich Corp.)(24.8 g, 66.0 mmol), PdCl2 (dppf).CH2Cl2 (2.45 g, 3.00 mmol), potassium carbonate (13.7 g, 13.7 mmol), water (60 mL) and THF (1.2 L) was refluxed under a nitrogen atmosphere for 16 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid, and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain Compound 16 (7.89 g, 15.0 mmol) in a yield of 50%.The physical properties of Compound 16 were as follows.1H-NMR (CDCl3, delta ppm): 7.81 (s, 2H), 7.06 (d, 2H), 6.97-7.04 (m, 4H), 6.70 (d, 2H), 3.64 (s, 6H), 2.80 (t, 4H), 1.56-1.63 (m, 4H), 1.32-1.41 (m, 12H), 0.90 (t, 6H)

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; Sumitomo Chemical Company Limited; US2011/87034; (2011); A1;,
Ester – Wikipedia,
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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. 2905-69-3, name is Methyl 2,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 2905-69-3

EXAMPLE 2 Dehalogenation of Methyl 2,5-Dichlorobenzoate A 50-mL round-bottom flask was equipped with a magnetic stir bar, reflux condenser, thermometer, nitrogen inlet, and heating mantle attached to a temperature controller. The flask was charged with methyl 2,5-dichlorobenzoate (5.0 g, 24 mmol) and copper powder (3.04 g, 48 mmol). Propionic acid (10 mL) and xylenes (15 mL) were added, and the resulting mixture was heated to 130-135 C. The reaction was monitored by GC analysis and was judged to be complete when the starting material was no longer detectable (3 hours). The reaction mixture was cooled to room temperature and filtered; the solids were washed with xylenes. The filtrates were blue-green. The filtrates were combined and washed with 1M hydrochloric acid solution until the blue-green color disappeared. The resulting yellow organic layer was washed with water and dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was dried under vacuum, yielding 3.93 g of methyl 3-chlorobenzoate as a pale yellow oil.

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

Reference:
Patent; Rohm and Haas Company; US5886210; (1999); 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., Safety of Methyl 4-amino-3,5-dichlorobenzoate

Example 45 Preparation of methyl 3,5-dichloro-4-cyanobenzoate (C77) Copper(I) cyanide (7.41 g, 82.7 mmol) was added to acetonitrile and heated to 80 C. for 30 minutes. tert-Butyl nitrite (10.5 g, 102 mmol) was added followed by methyl 4-amino-3,5-dichloro-benzoate (14.0 g, 63.6 mmol) in acetonitrile (200 mL) and the reaction mixture was stirred at 80 C. for 30 minutes. The reaction mixture was poured into an ammonia solution and extracted with petroleum ether to provide the title compound as an off-white solid (7.00 g, 43%): mp 98-101 C.; 1H NMR (400 MHz, CDCl3) delta 8.12 (s, 2H), 3.98 (s, 3H); ESIMS m/z 229 ([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; Dow AgroSciences LLC; LePlae, JR., Paul R.; Barton, Thomas; Gao, Xin; Hunter, Jim; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (147 pag.)US2017/210723; (2017); A1;,
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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. 1150164-80-9, name is Ethyl 2,2-difluoro-2-(2-methoxyphenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 2,2-difluoro-2-(2-methoxyphenyl)acetate

General procedure: To a solution of an appropriate ethyl alpha,alpha-difluoroaryl acetate (1.0 eq.) in MeOH (0.33 M) was added 1 M aq. K2CO3 (3.0 eq.). The reaction mixture was stirred at room temperature for 12 h before diluting with Et2O. The reaction mixture was extracted with aq. NaHCO3 (sat., 3x). The combined aqueous layers were acidified to pH 1 and extracted with Et2O (3x), then the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Products were purified by washing with n-pentane.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1150164-80-9.

Reference:
Article; Verhoog, Stefan; Pfeifer, Lukas; Khotavivattana, Tanatorn; Calderwood, Samuel; Collier, Thomas Lee; Wheelhouse, Katherine; Tredwell, Matthew; Gouverneur, Veronique; Synlett; vol. 27; 1; (2016); p. 25 – 28;,
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Some common heterocyclic compound, 762-42-5, name is Dimethyl but-2-ynedioate, molecular formula is C6H6O4, 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. Formula: C6H6O4

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762-42-5, its application will become more common.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
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Reference of 25081-39-4,Some common heterocyclic compound, 25081-39-4, name is Methyl 3,5-dimethylbenzoate, molecular formula is C10H12O2, 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 2 Preparation of methyl-3,5-bis(bromomethyl)-benzoate A solution of methyl-3,5-dimethyl-benzoate (16.8 g, 0.10 mol) in carbon tetrachloride (150 ml) was treated with N-bromosuccinimide (35.6 g, 0.20 mmol), and benzoyl peroxide (500 mg, cat. amount), and heated to reflux. After 3 hours, the mixture was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was concentrated under reduced pressure and recrystallized from diethyl ether/hexanes (1:1) to yield the product (18.0 g, 55% yield) as a granular white solid. mp 64-70C. (lit. mp 65-69 C.); TLC (20% ethyl acetate/hexanes): Rf =0.65 (UV active, CAM stain)

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Trustees of Columbia University in the City of New York; US5342934; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 77820-58-7, 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. 77820-58-7, name is Methyl 2-amino-3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 97 Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloroanthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for five hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15% sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67% yield, mp 56-68 C. IR and 1 H NMR spectra were in agreement with the assigned structure. Analysis: Calculated for C7 H8 ClNO: C, 53.35; H, 5.12; N, 8.88. Found: C, 53.16; H, 4.84; N, 9.28.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-3-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Dow Chemical Company; US4818273; (1989); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 29006-01-7, The chemical industry reduces the impact on the environment during synthesis 29006-01-7, name is Methyl 4-methoxybutanoate, I believe this compound will play a more active role in future production and life.

8-1. Preparation of Intermediate beta-Diketone Compound 1.8 mol of sodium hydride was added to the solvent ethylene glycol dimethyl ether, and 1 mol of methyl 4-methoxybutanoate was added thereto and stirred at room temperature for 10 minutes. Then, 1.2 mol of t-butylmethylketone was added to the solution which was then stirred at 92 C. for 19 hours. Then, the solution was cooled to room temperature and quenched in 36% hydrochloric acid, after which water and dimethylether were added to and mixed with the solution, and water was removed therefrom. The resulting organic material was washed with 1 wt % sodium hydroxide and then with saturated saline and concentrated, and the residue was fractionated, thereby obtaining the intermediate 8-methoxy-2,2-dimethyloctan-3,5-dione at a yield of 14%.

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, Methyl 4-methoxybutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHO, Youn-Joung; WADA, Senji; CHOI, Jung-Sik; LEE, Jin-Seo; SAKURAI, Atsushi; CHO, Kyoo-Chul; YOSHINAKA, Atsuya; SATO, Haruyoshi; UEYAMA., Junji; YOSHINO, Tomoharu; SHIMIZU, Masako; US2012/251724; (2012); A1;,
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Application of 13078-21-2, 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. 13078-21-2, name is Ethyl 2-(2-methoxyphenoxy)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

rytftro-l-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-l,3- propanediol (2h): (0183) (0184) 2h (0185) Scheme 9. Synthesis of ?’r_yi zro-l-(4-hydroxy-3-methoxyphenyl)-2-(2- methoxyphenoxy)– 1 ,3-propanediol (2h). (0186) This compound was prepared according to the same literature procedure as for compound 2g. Spectral data were consistent with those reported in the literature. JH NMR (400 MHz, CDC13) delta 7.16 (dd, J = 8.2, 1.6 Hz, 1H), 7.04-6.86 (m, 5H), 6.86 (d, J = 8.2 Hz, 1H), 5.71 (b s 1H), 4.96 (d, J = 7.9 Hz, 1H), 4.06-3.97 (m, 1H), 3.90 (s, 3H), 3.87 (s, 3H), 3.73-3.58 (m, 2H), 3.48 (ddd, J = 12.0, 7.8 and 3.6 Hz, 1H), 2.78-2.73 (m, 1H). HRMS (ESI) calculated for CnHzoOeNa [M + Na]+ 343.1158, found 343.1154.

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 2-(2-methoxyphenoxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; STAHL, Shannon, S.; COON, Joshua; RAHIMI, Alireza; ULBRICH, Arne; WO2015/138563; (2015); A1;,
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