3,4,5-Trimethoxybenzoic Acid → HCID 19866343, compound

Participants

Reaction Steps

19 g of chloromethyl chlorosulphate in 30 ml of methylene chloride are introduced dropwise at room temperature into a stirred mixture of 21.1 g of 3,4,5-trimethoxybenzoic acid, 33.6 g of sodium hydrogen carbonate and 3.4 g of tetrabutylammonium hydrogen sulphate in 600 ml of methylene chloride-water (1:1). In order to complete the reaction, the mixture is stirred at room temperature for a further 2 hours, the two phases are then separated, the aqueous phase is washed with 100 ml of methylene chloride and the combined organic phases are dried over sodium sulphate. The solvent is removed in a vacuum and the residue is chromatographed over 450 g of silica gel with methylene chloride. Fractions containing the product are evaporated and the residue is crystallized from methylene chloride-petroleum ether. 10.5 g of chloromethyl 3,4,5-trimethoxybenzoate are obtained as colourless needles with a melting point of 85°-86°. RF (silica gel/methylene chloride): 0.45.

Provenance & Evidence