Ethanol → 5-phenyl-4-pentyn-1-ol

Participants

Reaction Steps

A mixture of 1-phenyl-5-tetrahydropyranyloxypent-1-yne (0.2 g), absolute ethanol (4 ml) and p-toluenesulphonic acid (20 mg) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (40 ml) and extracted with ether (2×20 ml). The ether extracts were washed with saturated NaHCO3 solution, dried over MgSO4 and purified by chromatography on silica (20 g), eluting with 10% ether in hexane grading to 100% ether, followed by 10% ethyl acetate in ether. The solvent was removed to give 5-phenylpent-4-yn-1-ol as a colourless oil.

Provenance & Evidence