Category: esters-buliding-blocks

Electric Literature of 25081-39-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25081-39-4 name is Methyl 3,5-dimethylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

3-Bromomethyl-5-methyl-benzoic acid methyl ester (LW003036B) and 3,5-Bis- bromomethyl-benzoic acid methyl ester (LWO03036C); To a solution of methyl 3,5-dimethylbenzoate (15.0 g, 89.52 mmol) in carbon tetrachloride (molecular sieves 4 A dried, 150 mL) was added finely powdered N- bromosuccinimide (16.1 g, 89.52 mmol) and benzoyl peroxide (> 97%, 200 mg). The light yellow suspension was then refluxed which turned into a light orange suspension after about 10 min. When the colour of the suspension returned to light yellow again about 45 min later, the reflux was terminated. After cooling to room temperature, the suspension was filtered and the filter cake collected was washed with ether (5 x 30 mL). The combined filtrates were evaporated to give a clear bright yellow liquid (22.9 g) which was fractionated by flash chromatography (silica: 700 g; eluent: ethyl acetate/hexane, 1 : 10 to 1 : 1). The second fraction that collected upon evaporation gave LW003036B as a translucent pale yellow oil (13.32 g, 54.79 mmol, 61%) whereas the third fraction gave LW003036C as white fluffy needle-shaped crystals (1.99 g, 3.08 mmol, 7%). LW003036B: Rf: 0.27 (ethyl acetate/hexane, 1: 8), c. f. 0.39 (S.M.) No.H (270 MHz, CDC13) 2.39 (3H, s, Ar-CH3), 3.90 (3H, s, COOMe), 4.47 (2H, s, CH2Br), 7.39 (1H, slightly broad s, Ar), 7.78 (1H, slightly broad s, Ar) and 7.85 (1H, s, Ar). LRMS (FAB+): 443.3 (17), 398.3 [25, (M81Br+H+NBA) +], 243.1 [100, (M79Br+H)+], 163.1 [83, (M79Br-79Br) +], 85.1 (54). HRMS (FAB+) : 243.00124 C10H12O2Br requires 243.00207 LW003036C: Rf: 0.20 (ethyl acetate/hexane, 1:8), c.f. 0.39 (S.M.) m. p. 100-103 C [Lit.l (from column), 95-97 C] (at) Liu P, Chen Y, Deng J, Tu Y. An efficient method for the preparation of benzylic bromides. Synthesis 2001,14: 2078- 2080. No.H (400 MHz, CDC13) 3.93 (3H, s, OCH3), 4.49 (4H, s, 2 x CH2), 7.60 (1H, t, J- 1.7 Hz, C4-H) and 7.97 (2H, d, J- 2.0 Hz, C2-H and C6-H).; 3-Bromomethyl-5-methyl-benzoic acid methyl ester (LW003015B) and 3,5-Bis- bromomethyl-benzoic acid methyl ester (LWO03015C); To a solution of methyl 3,5-dimethylbenzoate (5.57 g, 33.24 mmol) in carbon tetrachloride (molecular sieves 4 A dried, 50 mL) was added finely powdered N- bromosuccinimide (5.98 g, 33.24 mmol) and benzoyl peroxide (No. 97%, 100 mg). The light yellow suspension was then refluxed which turned into a light orange suspension after about one hour. When the colour of the suspension returned to light yellow again about 30 min later, the reflux was terminated. After cooling to room temperature, the suspension was filtered and the filter cake collected was washed with ether (5 x 30 mL). The combined filtrates were evaporated to give a clear bright yellow liquid (8.15 g) which was fractionated by flash chromatography (silica: 300 g; eluent: ethyl acetate/hexane, 1 : 10; flow rate: ca. 30 mL/min). The first fraction collected was the starting material (998 mg). The second and third fractions collected were respectively LW003015B as a translucent pale yellow oil (4.90 g, 20.16 mmol, 61%) and LW003015C as white fluffy needle-shaped crystals (990 mg, 3.08 mmol, 9%). LW003015B Rf: 0.27 (ethyl acetate/hexane, 1: 8), c. f. 0.39 (S.M.) No.H (270 MHz, CDC13) 2.39 (3H, s, Ar-CH3), 3.90 (3H, s, COOMe), 4.47 (2H, s, CH2Br), 7.39 (1H, slightly broad s, Ar), 7.78 (1H, slightly broad s, Ar) and 7.85 (1H, s, Ar). LRMS (FAB+) : 443.3 (17), 398.3 [25, (M81Br+H+NBA) +], 243.1 [100, (M79Br+H)+], 163.1 [83, (M79Br-79Br) +], 85.1 (54). HRMS (FAB+): 243.00124 ClOH1202Br requires 243.00207. LW003015C Rf: 0.20 (ethyl acetate/hexane, 1: 8), c. f. 0.39 (S.M.) m. p. 100-103 C [Lit. (at) (from column), 95-97 C] (at) ¹ Liu P, Chen Y, Deng J, Tu Y. An efficient method for the preparation of benzylic bromides. Synthesis 2001,14: 2078- 2080. No.H (400 MHz, CDC13) 3.93 (3H, s, OCH3), 4.49 (4H, s, 2 x CH2), 7.60 (1H, t, J- 1.7 Hz, C4-H) and 7.97 (2H, d, J- 2.0 Hz, C2-H and C6-H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,5-dimethylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; STERIX LIMITED; WO2005/118560; (2005); A1;,
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Application of 1070-64-0,Some common heterocyclic compound, 1070-64-0, name is Ethyl 6,8-dichlorooctanoate, molecular formula is C10H18Cl2O2, 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.

600 kg (2.48 kmol) racemic 6,8-dichloroethyl caprylate and 78 kg (2.43 kmol, 0.98 equiv.) sulphur in 576 kg ethanol were placed in a 6 m3 reactor with stirrer, metering pump, pressure and internal temperature measurement and also jacket heating. At an internal temperature of 110 C. and a pressure of 0.35 MPa, 2062 kg of an aqueous sodium sulphide solution (12.3 wt. %) comprising 253.6 kg Na2S (3.24 kmol, 1.31 equiv.) was metered in uniformly with stirring over a period of 85 min. The reaction mixture was stirred for another 120 min at 110 C. Then 508 g of a solution of sodium borohydride (12 wt. %) in sodium hydroxide solution (40 wt. %) comprising 61.0 kg NaBH4 (1.61 kmol, 0.65 equiv.) was metered in uniformly within 90 min. at 70 C. The ethanol contained was distilled off from the reaction mixture to the greatest possible extent, and thereupon a further 253 kg of a solution of sodium borohydride (12 wt. %) in sodium hydroxide solution (40 wt. %) comprising 30.4 kg NaBH4 (0.80 kmol, 0.32 equiv.) added over a period of 60 min. at 70 C. Once addition had taken place, the mixture was heated to boiling and stirred further for 30 min. at this temperature. After cooling, 540 kg MTBE was added and the batch was acidified to a pH value of 2.6 to 3.0 by adding 1454 kg (12.3 kmol) hydrochloric acid (31 wt. %). The organic phase was separated off and the organic solvent was distilled off completely without a vacuum. 506 kg of a yellow liquid was obtained, with a content of 94.0 wt. % dihydrolipoic acid and a polymer content of 5.6 wt. % (corresponds to a yield of 91.8% of theory).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6,8-dichlorooctanoate, its application will become more common.

Reference:
Patent; ALZCHEM TROSTBERG GMBH; SCHNAPPERELLE, Ingo; WINKLER, Stephan; SANS, Juergen; THALHAMMER, Franz; (7 pag.)US2019/276396; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1202-25-1, The chemical industry reduces the impact on the environment during synthesis 1202-25-1, name is Methyl 4-dimethylaminobenzoate, I believe this compound will play a more active role in future production and life.

PREPARATION 10i 1-(4-N,N-Dimethylaminophenyl)-1-methylethylamine Following a procedure similar to that described in Preparation 10a, but using methyl 4-N,N-dimethylaminobenzoate as a starting material, in a relative amount similar to that used in that Preparation, the title compound was obtained in a yield of 48%. Nuclear Magnetic Resonance Spectrum (CDCl3), delta ppm: 1.48 (6H, singlet); 1.70 (2H, broad singlet); 2.95 (6H, singlet); 6.65-6.80 (2H, multiplet); 7.30 (2H, doublet, J=9 Hz). Infrared Absorption Spectrum (liquid film), numax cm-1: 2960, 1615, 1525, 815.

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-dimethylaminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sankyo Company, Limited; US5536714; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 850449-93-3, name is Methyl 2-(5-amino-2-methylphenyl)acetate, molecular formula is C10H13NO2, 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-(5-amino-2-methylphenyl)acetate

6-Chloro-4-phenylamino-pyridine-3-carbaldehyde 18 (21 mg, 0.09 mmol) is mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (18 mg, 0.1 mmol) and potassium carbonate (37 mg, 0.27 mmol) in DMF (2 mL). The mixture is heated to 100 0C for 16 h. After cooling to rt and removing solvent in vacuo, the crude product is purified using flash chromatography (hexane : ethyl acetate = 1 : 1). The title compound 3-(5-amino- 2-methyl-phenyl)-7-chloro-l-phenyl-lH-[l,6]naphthyridin-2-one 19 is obtained as a pale solid. 1H NMR (400MHz, CDCl3) delta 8.53 (s, IH), 7.68 (s, IH), 7.53-7.57 (m, 2H), 7.47 -7.51 (dt IH), 7.20-7.23 (m, 2H), 6.96 (d, IH), 6.59 (dd, IH), 6.58 (s, IH), 6.52 (s, IH), 2.05 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 850449-93-3, its application will become more common.

Reference:
Patent; IRM LLC; WO2008/51757; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1732-08-7, name is Dimethyl pimelate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1732-08-7, Application In Synthesis of Dimethyl pimelate

Dimethyl pimelate (3.76 g, 20 mmol) was added dropwise to a suspension of NaH(1.06g, 26.6 mmol, 60% in mineral oil) in dry THF (20 mL). The resulting slurry wasstirred at RT overnight. The reaction was quenched with water (5 mL), extracted withEtOAc (20 mL× 3), washed with brine, dried (Na2SO4), and concentrated undervaccum. The residue was chromatographed with petrolum ether-EtOAc (20:1) to give the desired methyl 2-cyclohexanonecarboxylate as a colorless oil. (2.42 g, 77%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Qian, Hua; Gu, Guoxian; Zhou, Qinghai; Lu, Jiaxiang; Chung, Lung Wa; Zhang, Xumu; Synlett; vol. 29; 1; (2018); p. 51 – 56;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, 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. COA of Formula: C6H12O3

Starting material 209a (9.9 g, 75 mmol) was dissolved in THF (100 mL) and water (25 mL). LiOH (3.4 g, 80.9 mmol), the resulting mixture was stirred at room temperature overnight. 1 N HCl (100 mL) was added and extracted with EtOAc. The organic extracts were combined, washed with brine, dried (MgSO4) to give compound 209b (8.8 g, 93%).

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

Reference:
Patent; Schering Corporation; US2006/264489; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 6065-54-9, 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. 6065-54-9, name is Dimethyl 2,2-dimethylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. 2,2-Dimethyl-3-oxo-3-(pentylamino)propionic acid Following the procedure of Example 1A and B except substituting dimethyl 2,2-dimethylmalonate for dimethyl malonate, the title compound is obtained.

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, Dimethyl 2,2-dimethylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4654356; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 204707-42-6, name is Methyl 4-fluoro-2-methoxybenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H9FO3

Step 2: Combine the product of Step 1 (1.43 g, 7.2 mmol) and iron powder (0.018 g) in CH2Cl2 (15 ml ). Add dropwise Br2 (0.44 ml, 8.7 mmol) in CH2Cl2 (5 ml). Stir 18 h and wash with water, then 1N NaOH. Dry (MgSO4) and concentrate to obtain the bromide as a yellow solid

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; Schering Corporation; US2004/220194; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 87661-20-9 as follows. Formula: C8H14O2

Example 73 (2S)-1-({1-[2-(2-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60 starting from 4-chloromethyl-5-methyl-2-(2-chloro-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. Steps A] and C] were performed as outlined in example 60, step B] was done according to example 69. The title compound was obtained as a light brown gum. MS (ISP): 399.3 (MH+) and 401.4 (MH+).

According to the analysis of related databases, 87661-20-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1462-12-0, name is Diethyl 2-ethylidenemalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H14O4

Synthesis of compound 9.4. To a solution of compound 9.3 (1.3g, 4.86mmol, 1.0 equiv) and diethyl 2-ethylidenemalonate (0.9 g, 4.86mmol, 1.0 equiv) in ethanol (13 mL) was added sodium ethoxide (0.59g, 8.74mmol, 1.8 equiv) at room temperature. The mixture was refluxed for 3 hours then the solvent was removed under reduced pressure. The crude material was purified via flash column chromatography to yield compound 9.4 (2.6g, 65%>). MS (ES): m/z 409 [M+H]+.

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

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics