Benzoic acid, 2-[(trimethylsilyl)methyl]-

Base Information

• Chemical Name: Benzoic acid, 2-[(trimethylsilyl)methyl]-
• CAS No.: 71435-93-3
• Molecular Formula: C11H16O2Si
• Molecular Weight: 208.332
• Mol file: 71435-93-3.mol

Synonyms:

Chemical Property of Benzoic acid, 2-[(trimethylsilyl)methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 2-[(trimethylsilyl)methyl]-

There total 2 articles about Benzoic acid, 2-[(trimethylsilyl)methyl]- 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: 77.0%

ortho-methylbenzoic acid (118-90-1) + chloro-trimethyl-silane (75-77-4) → o-<(trimethylsilyl)methyl>benzoic acid (71435-93-3)

Guidance literature:

ortho-methylbenzoic acid; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h; Inert atmosphere;

With 2,2,6,6-tetramethyl-piperidine; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.078

Reference yield:

2-chloro[(trimethylsilyl)methyl]benzene (68307-67-5) → o-<(trimethylsilyl)methyl>benzoic acid (71435-93-3)

Guidance literature:

With lithium; folgende Umsetzung mit CO₂;

DOI:10.1039/jr9540000939

Reference yield: 88.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + o-<(trimethylsilyl)methyl>benzoic acid (71435-93-3) → 4-nitrophenyl 2-[(trimethylsilyl)-methyl] benzoate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b03544

upstream raw materials:

2-chloro[(trimethylsilyl)methyl]benzene

ortho-methylbenzoic acid

chloro-trimethyl-silane

Downstream raw materials:

<(6-Carbomethoxy-1.4-cyclohexadien-1-yl)methyl>trimethylsilan

2-[(trimethylsilyl)methyl]benzyl alcohol

o-<(trimethylsilyl)methyl>benzoyl chloride

2-(1-Trimethylsilanyl-hex-5-enyl)-benzoic acid

Refernces

• 1、 Das, Manas,O'Shea, Donal F.. "Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents". . p. 6448 - 6460. Retrieved 2013/07/26.