Acetic Anhydride → 1,3-Dipivaloyl-2-acetoxymethyl glycerol

Participants

Reaction Conditions

Reaction Steps

50 g of 1,3-dipivaloyl-2-methoxymethyl glycerol, 150 ml of methylene chloride, and 17 ml of acetic anhydride was cooled to about -5° C. Then 0.3 ml of boron trifluoride etherate was added and the mixture was stirred for an additional 1 hr at about 0° C. then allowed to warm to 25° C. over an additional 1.5 hr. After this period, 100 ml saturated aqueous Na2Cl3 was added to the mixture followed by 100 ml CH2Cl2. After vigorous stirring for 5 min, the organic layer was separated and washed once with 100 ml H2O, once with aqueous NaCl, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 1,3-dipivaloyl-2-acetoxymethyl glycerol as a faintly colored oil.

Provenance & Evidence