Methanesulfonyl chloride → Methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester

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Reaction Steps

8 g. of α-methyl-1-phenyl-2,5-cyclohexadien-1-ethanol are dissolved in 50 ml. of pyridine and 6.4 g. of mesyl chloride are added dropwise at 0°-5° C. After stirring at room temperature for 2 hours, the mixture is worked-up as follows: The mixture is treated with ice-water and extracted with ether. The ether phase is washed with 3 N aqueous hydrochloric acid, then washed neutral, dried and concentrated. The crude product obtained is chromatographed on 100 g. of silica gel with ether/petroleum ether (1:1). There is obtained an oily product which crystallizes in the cold. After crystallization from methylene chloride/hexane, there is obtained methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester having a melting point of 51°-53° C.

Provenance & Evidence