Methanol → 2,2-dimethoxycyclopentanol

Participants

Reaction Conditions

Reaction Steps

A solution of cyclopentanone (11.6 ml, 130 mmol) in methanol (250 ml) was added drop-wise at 0° C. over 20 minutes to a stirred solution of potassium hydroxide (85% tech., 22.1 g, 335 mmol) in methanol (75 ml). The mixture was stirred at 0° C. for 30 minutes then 2-iodosylbenzoic acid (36.45 g, 138 mmol) was added in portions over 1 hour. The mixture was allowed to warm to ambient temperature over 4 hours, then stirred at ambient temperature for 20 hours. The majority of solvent was removed in vacuo then the product was extracted into dichloromethane (400 ml), then the extracts were washed with water (2×250 ml), dried (Na2SO4) and the solvent removed in vacuo to leave 2,2-dimethoxycyclopentanol as a colourless oil (11.98 g) which was used without further purification.

Provenance & Evidence