Acetic Acid → 5,5-Diethyldihydrofuran-2(3h)-one

Participants

Reaction Conditions

Reaction Steps

Succinic anhydride (15.0 g, 150 mmol, 1.0 eq) was added into a round bottomed flask, and the flask was flushed with nitrogen. THF (500 mL) was then added via a syringe. The solution was cooled to 0° C. Methyl magnesium bromide in ether (3.0 M, 100 mL, 300 mmol, 2.0 eq) was added via syringe slowly. The reaction mixture was warmed to room temperature gradually, and then heated to 50° C. for 12 hours. A yellow solution was formed. After cooling the reaction mixture to room temperature, AcOH was added until pH=4, and stirring was continued for an additional 12 hours. Water (75 mL) was added, and THF and ether were removed under reduced pressure. The green suspension was extracted with CH2Cl2 (60 mL×5), and the organic phase was dried over anhydrous Na2SO4 and concentrated. Purification by vacuum distillation gave the product as brown oil (9.7 g, 46%). This compound has been synthesized using several different methods in the literature.

Provenance & Evidence