Carbon Tetrachloride → 2-Chloro-4-(oxan-4-yl)phenol

Participants

Reaction Steps

10 ml of sulfuryl chloride were added with stirring to a mixture of 14.1 g of 4-(p-hydroxyphenyl)-tetrahydropyran and 40 ml of carbon tetrachloride and the mixture was heated to 45°-50° C for 16 hours. The mixture was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with methylene chloride yielded a crystal product which was dissolved in 200 ml of N sodium hydroxide and the solution was washed with ether and acidified with 2N hydrochloric acid. The mixture was extracted with ether and the organic phase was washed with water, then an aqueous sodium bisulfite solution and then with water. The extracts were dried and evaporated to dryness to obtain 6.4 g of 4-(4-hydroxy-3-chlorophenyl)-tetrahydropyran melting at 123°-125° C.

Provenance & Evidence