Ethyl 2-bromopropionate → Ethyl 2-[4-(oxan-4-yl)phenoxy]propanoate

Participants

Reaction Steps

A suspension of 8.9 g of 4-(p-hydroxyphenyl)-tetrahydropyran in 50 ml of ethanol was added to a mixture of 1.15 g of sodium in 100 ml of ethanol and the mixture was stirred for 2 hours at room temperature and was then cooled to 0° C. 7.82 ml of ethyl 2-bromo-propanoate were added to the mixture which was then allowed to return to room temperature and the mixture was refluxed for 5 hours. The mixture was evaporated to dryness and the residue was dissolved in a mixture of 100 ml of ether, 45 ml of water and 5 ml of 2N hydrochloric acid. The aqueous phase was removed by decanting and the organic phase was washed with 2N sodium hydroxide, was dried and evaporated to dryness under reduced pressure to obtain 7.9 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoate with a boiling point of 138°-140° C at 0.05 mm Hg.

Provenance & Evidence