2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester

Base Information

• Chemical Name: 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester
• CAS No.: 135790-17-9
• Molecular Formula: C₂₄H₂₆O₃S
• Molecular Weight: 394.535
• Mol file: 135790-17-9.mol

Synonyms:2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester

Chemical Property of 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester

There total 2 articles about 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl 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: 70.0%

(2R,5S)-trans-4,4-diphenyl-5-methyl-1,3,2-dioxathiolane 2-oxide (126577-49-9) + 2-mesitylmagnesium bromide (2633-66-1) → 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester (135790-17-9) + 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1,1-diphenyl-propyl ester (135790-16-8)

Guidance literature:

In tetrahydrofuran; at -78 ℃; Yields of byproduct given;

DOI:10.1021/jo00021a008

Reference yield:

(S)-1,1-diphenyl-1,2-propanediol (46755-94-6) → 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester (135790-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / SOCl₂, triethylamine / CH₂Cl₂ / -40 °C

2: 70 percent / tetrahydrofuran / -78 °C

With thionyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00021a008

Reference yield: 87.0%

(R)-methyl mesityl sulfoxide (18689-86-6) + 2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester (135790-17-9) → (S,S)-1,1-bis-(mesitylsulfinyl)-methane (1246464-35-6)

Guidance literature:

(R)-methyl mesityl sulfoxide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere;

2,4,6-Trimethyl-benzenesulfinic acid (S)-2-hydroxy-1-methyl-2,2-diphenyl-ethyl ester; In tetrahydrofuran; hexane; at 0 ℃; for 0.416667h; Inert atmosphere;

DOI:10.1016/j.tetasy.2010.04.023

upstream raw materials:

(2R,5S)-trans-4,4-diphenyl-5-methyl-1,3,2-dioxathiolane 2-oxide

2-mesitylmagnesium bromide

(S)-1,1-diphenyl-1,2-propanediol

Downstream raw materials:

(R)-methyl mesityl sulfoxide

(S,S)-1,1-bis-(mesitylsulfinyl)-methane