(S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile

Base Information

• Chemical Name: (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile
• CAS No.: 136983-96-5
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• Mol file: 136983-96-5.mol

Synonyms:(S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile

Chemical Property of (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile

There total 20 articles about (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile 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: 95.0%

potassium cyanide + acetic anhydride (108-24-7) + 4-methyl-benzaldehyde (104-87-0) → (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile (136983-96-5)

Guidance literature:

With 2C₂H₅O₄S^(1-)*C₇₂H₁₀₄N₄O₁₆V₂⁽²⁺⁾; water; tert-butyl alcohol; In dichloromethane; at -20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.07.005

Reference yield: 90.0%

Acetyl cyanide (631-57-2) + 4-methyl-benzaldehyde (104-87-0) → (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile (136983-96-5)

Guidance literature:

With Ti-(R,R)-3,5-t-Bu₂-salen; triethylamine; In dichloromethane; at -40 ℃; for 10h;

DOI:10.1021/ja052804q

Reference yield: 87.0%

(S)-2-hydroxy(4-methylphenyl)acetonitrile (4815-10-5,10017-04-6,58634-14-3,105452-15-1) + acetyl chloride (75-36-5) → (S)-2-acetyloxy-2-(4-methylphenyl)acetonitrile (136983-96-5)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/chem.200701660

upstream raw materials:

Isopropenyl acetate

2-hydroxy-2-(4-methylphenyl)acetonitrile

4-methyl-benzaldehyde

2-hydroxy-2-methylpropanenitrile

Downstream raw materials:

(S)-2-hydroxy(4-methylphenyl)acetonitrile

Refernces

• 1、 Tan, Chunxia,Han, Xing,Li, Zijian,Liu, Yan,Cui, Yong. "Controlled Exchange of Achiral Linkers with Chiral Linkers in Zr-Based UiO-68 Metal-Organic Framework". supporting information. p. 16229 - 16236. Retrieved 2018/11/27.
• 2、 Li, Jiawei,Ren, Yanwei,Qi, Chaorong,Jiang, Huanfeng. "The first porphyrin-salen based chiral metal-organic framework for asymmetric cyanosilylation of aldehydes". supporting information. p. 8223 - 8226. Retrieved 2017/07/24.