25436-27-5

Upstream product

• 1126-46-1 Methyl 4-chlorobenzoate 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 74-11-3 para-chlorobenzoic acid 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 790-41-0 4-chlorobenzoic anhydride 
• 74-11-3 para-chlorobenzoic acid 
• 70152-88-4 Hexadecyl-p-chlorbenzoat 
• 70153-23-0 Eicosyl-p-chlorbenzoat 
• 5458-41-3 C₁₈H₂₇ClO₂ 
• 623-03-0 4-Cyanochlorobenzene 

Relevant academic research and scientific papers

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Synthesis of trimethylsilyl carboxylates by HMDS under solvent-free conditions

A broad set of structurally different carboxylic acids were transformed into their trimethylsilyl esters with HMDS in a practically completely solvent-free process, while a catalytic amount of iodine was required in some cases. The process has several advantages over the known methods: untreated reactants, air atmosphere, mild and neutral conditions, no evolution of hydrogen halide, no need of an additional base, low amount of waste, completely without chromatography, low consumption of energy, and operational simplicity.

Dealkylation of esters via treatment with N-(trimethylsilyl) diethylamine and methyl iodide

A method for the conversion of esters to carboxylic acids has been reported. Reaction of methyl o-methoxybenzoate with N-(trimethylsilyl)diethylamine and methyl iodide, followed by hydrolysis, afforded o-methoxybenzoic acid with a 94% yield based on 96% conversion. Methyl esters of not only aromatic acids but also aliphatic acids were converted to the corresponding acids with high yields. A combination of N-(trimethylsilyl)dimethylamine and methyl iodide was also effective to give p-methylbenzoic acid with a 85% yield based on 90% conversion from the corresponding methyl ester.