Hydrochloric Acid → p-Toluenesulfonic acid

Participants

Reaction Conditions

Reaction Steps

11.6 g of triethylamine and then 21.9 g of p-toluene sulfonyl chloride were added at -50° C under an inert atmosphere to a mixture of 11.6 g of (R) allethrolone in 100 ml of tetrahydrofuran and the mixture was stirred for 48 hours at 5° C after which it was poured with stirring into aqueous 0.1N hydrochloric acid solution. The aqueous phase was extracted with chloroform and the organic extracts were washed with water, dried and evaporated to dryness. The 29 g of residue was chromatographed over silica gel and was eluted with a 95-5 benzene-ethyl acetate mixture to obtain 6.8 g of p-toluene sulfonate of (R) allethrolone.

Provenance & Evidence