Benzaldehyde → alpha-Ethynylbenzenemethanol

Participants

Reaction Steps

To a solution of 2.65 g of benzaldehyde (Formula 26) in 50 mL of THF at room temperature was added 100 mL of 0.5M ethynylmagnesium bromide in THF. The mixture was stirred at room temperature for 2 hours. Then, the mixture was diluted with diethylether and a saturated solution of ammonium chloride. The mixture was extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (20% ethyl acetate/hexane) gave 3.17 g of 1-phenyl-prop-2-yn-1-ol (Formula 27) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.68 (m, 1H), 5.46-5.49 (m, 1H), 7.34-7.43 (m, 3H), 7.55-7.57 (m, 2H).

Provenance & Evidence