Benzoic acid, 2-hydroxy-6-methyl-, cyanomethyl ester

Base Information

• Chemical Name: Benzoic acid, 2-hydroxy-6-methyl-, cyanomethyl ester
• CAS No.: 438187-09-8
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Mol file: 438187-09-8.mol

Synonyms:

Chemical Property of Benzoic acid, 2-hydroxy-6-methyl-, cyanomethyl ester

Chemical Property:

Purity/Quality:

99.00% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid, 2-hydroxy-6-methyl-, cyanomethyl ester

There total 3 articles about Benzoic acid, 2-hydroxy-6-methyl-, cyanomethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2-hydroxy-6-methylbenzoic acid (567-61-3) + chloroacetonitrile (107-14-2) → 2-hydroxy-6-methyl-benzoic acid cyanomethyl ester (438187-09-8)

Guidance literature:

With triethylamine; In acetone; for 3h; Heating;

DOI:10.1021/ja026025a DOI:10.1021/ja0352350

Reference yield:

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one (164014-40-8) → 2-hydroxy-6-methyl-benzoic acid cyanomethyl ester (438187-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 - 0 °C

1.2: 85 percent / MeI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C

2.1: 99 percent / KOH / tetrahydrofuran; H₂O / Heating

3.1: 80 percent / Et₃N / acetone / 3 h / Heating

With potassium hydroxide; triethylamine; In tetrahydrofuran; diethyl ether; water; acetone;

DOI:10.1021/ja0352350

Reference yield:

2, 2, 5-trimethyl-4H-benzo[d][1,3]dioxin-4-one (438187-08-7) → 2-hydroxy-6-methyl-benzoic acid cyanomethyl ester (438187-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / KOH / tetrahydrofuran; H₂O / Heating

2: 80 percent / Et₃N / acetone / 3 h / Heating

With potassium hydroxide; triethylamine; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja0352350

upstream raw materials:

2-hydroxy-6-methylbenzoic acid

chloroacetonitrile

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

2, 2, 5-trimethyl-4H-benzo[d][1,3]dioxin-4-one

Downstream raw materials:

2-(tert-butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid cyanomethyl ester

2-bromomethyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid cyanomethyl ester

2-[6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enyl]-6-hydroxy-benzoic acid cyanomethyl ester

2-(tert-butyl-dimethyl-silanyloxy)-6-[6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enyl]-benzoic acid cyanomethyl ester

Refernces

• 1、 Shen, Ruichao,Lin, Cheng Ting,Bowman, Emma Jean,Bowman, Barry J.,Porco Jr., John A.. "Lobatamide C: Total synthesis, stereochemical assignment, preparation of simplified analogues, and V-ATPase inhibition studies". . p. 7889 - 7901. Retrieved 2007/10/03.