Acetic Acid → 4-Methylene-3-oxabicyclo[3.2.1]octan-2-one

Participants

Reaction Steps

98.7 g (0.81 mol) of 3-methylenebicyclo[2.2.1]heptan-2-one and 32.9 g (0.24 mol) of sodium acetate trihydrate in 400 ml of dichloromethane are used as the initial charge in a reaction vessel. While controlling the temperature (CO2/acetone bath), 230 g of 32% peracetic acid in acetic acid (0.97 mol) are then added dropwise in the course of 2.5 hours, at a temperature of from −8° C. to −10° C. with stirring. The reaction mixture is subsequently stirred at a temperature of −8° C. for a further hour. 200 g of ice are then added, followed by 20 g (0.16 mol) of sodium sulfite in 100 ml of water. The organic phase is separated off and washed with water, dried over magnesium sulfate and concentrated to yield, in the form of a liquid residue, 81.9 g of 4-methylene-3-oxabicyclo[3.2.1]octan-2-one with a 93% content and a yield of 68.2%.

Provenance & Evidence