Water → 2-cyclobutyl-2-hydroxy-2-phenylacetic acid

Participants

Reaction Steps

To 1-cyclobutyl-1-phenyl-2-propin-1-ol (Compound (10), 5.80 g), water (20 ml) was added. Under stirring, an aqueous solution (300 ml) of potassium permanganate (14.0 g) was added dropwise to the resulting mixture at 0° C., followed by vigorous stirring for further 2 hours. Sodium sulfite was added to the reaction mixture at room temperature. The precipitate so obtained was filtered through Celite and the filtrate was extracted with ether. The organic layer was dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain the title compound (2.36 g, 36.8%)) as colorless prism.

Provenance & Evidence