Water → (1-Phenylcyclopentyl)methyl methanesulfonate

Participants

Reaction Steps

A solution of methanesulphonyl chloride (1.62 g) in dry dichloromethane (10 ml) was added over 20 minutes to a stirred mixture of 1-hydroxymethyl-1-phenylcyclopentane (1.91 g) and triethylamine (1.64 g) in dry dichloromethane (50 ml) at 0° C. (white precipitate). After 1 hour, all at about 0° C., water was added to the reaction mixture and the organic and aqueous layers were separated. The organic layer was washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate and water, then dried over magnesium sulphate and concentrated to give almost pure 1-methanesulphonyloxymethyl-1-phenylcyclopentane (2.85 g) as an almost colourless oil which crystallised completely on standing in the fridge, melting point 55°-60° C., 1H n.m.r. (CDCl3): δ 2.51 (3H, s, CH3SO2), 4.16 (2H, s, CH2OSO2CH3).

Provenance & Evidence