Hydrochloric Acid → HCID 178496940, compound

Participants

Reaction Steps

28.26 g of aluminium trichloride are suspended in 70 ml of dichloromethane and, over a period of 15 minutes, 10.19 g of 5-methoxybenzocyclobutene-1-carboxylic acid methyl ester are added dropwise at from 20° to 30°. Stirring is carried out for 30 minutes, 20.8 g of m-methylthiobenzoyl chloride are added dropwise over a period of 20 minutes and the whole is stirred for 4 hours at room temperature, poured into a mixture of 200 g of ice, 20 ml of concentrated hydrochloric acid and 200 ml of water, stirred for 30 minutes and extracted by shaking twice with 50 ml of dichloromethane each time and once with 50 ml of a mixture of trichloromethane and methanol (3:1). The organic phases are combined, washed twice with water, dried over magnesium sulphate, treated with kieselguhr and concentrated by evaporation. Chromatography over silica gel using hexane/ethyl acetate (4:1) as eluant yields 4-(m-methylthiobenzoyl)-5-hydroxybenzocyclobutene-1-carboxylic acid methyl ester in the form of a yellow oil.

Provenance & Evidence