Acetic Acid → Spiro[5.5]undec-1-en-3-one

Participants

Reaction Steps

To a solution of the above product (1) (22.6 g) in toluene (100 ml) was added methylvinyl ketone (9.6 g), and the mixture was stirred at room temperature. After 3 hours, to the reaction mixture were added sodium acetate (10 g), acetic acid (40 ml) and water (40 ml), and the mixture was heated under reflux. After 4 hours, the reaction mixture was cooled to room temperature and then ethyl acetate (100 ml) was added thereto. The mixture was washed with water (100 ml), 2 mol/l hydrochloric acid (50 ml) and then brine (100 ml), and the organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was distilled under reduced pressure (95° C., 1 mmHg) to give 4.3 g of spiro[5.5]undecen-3-one.

Provenance & Evidence