Diethyl Ether → 3-Hydroxy-2,2-bis(hydroxymethyl)propyl acetate

Participants

Reaction Steps

Pentaerythritol (9.5 grams, 0.07 mol), 7.0 grams (0.02 mol) of pentaerythritol tetraacetate and 500 mg of potassium carbonate were heated for 12 hours at 180° C. A light brown solution resulted which was boiled for 15 minutes in 50 ml of acetone and the resulting precipitate was filtered off. The filtrate was concentrated and passed through a plug of silica gel using acetone as a solvent. The mixture was purified by flash chromatography (1:1, CHCl3 :acetone) to yield a product of Rf =0.1. Addition of 25 ml of ether caused the product to solidify, yielding 4.6 grams of pentaerythritol monoacetate as a white solid.

Provenance & Evidence