Acetone → 2,6,6-Trimethylfulvene

Participants

Reaction Steps

A solution of 2-methyl-1,3-cyclopentadiene (125 g, 1.56 mol) in 1.2 L of ethanol was treated at low temperature with 126 mL (1.72 mol) of acetone and 142 mL (1.72 mol) of pyrrolidine. The resulting solution was kept below room temperature overnight. Then the reaction mixture was neutralized with a 10% aq. solution of H3PO4, extracted with hexane (3×150 mL) and washed with water until neutral pH. The organic phase was separated, dried with MgSO4 and concentrated. The residue was distilled at 70° C./60 mmHg. Yield 112.6 g (60%).

Provenance & Evidence