Hydrochloric Acid → 4-But-2-ynyloxy-benzenethiol

Participants

Reaction Steps

To a solution of 11.8 g (0.045 mol) of triphenylphosphine dissolved in 10 mL of dichloromethane and 0.3 mL of DMF was added 3.67 g (0.015 mol) of the 4-but-2-ynyloxy-benzenesulfonyl chlorid, dissolved in 15 mL of dichloromethane and the resulting mixture was stirred for 2 h at room temperature. After the addition of 5 mL of 1N HCl solution the reaction was stirred for 0.5 h followed by the addition of 15 mL of brine. The organics were separated and concentrated in vacuo and the residue was diluted with ether and 2.5N sodium hydroxide solution. The resulting precipitate was filtered off and the aqueous layer was acidified to pH 2 and extracted with ether. The combined organics were washed with brine, dried over Na2SO4, filtered through Magnesol® and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexanes/ether (4:1) to provide 1.13 g (42%) of the thiol as a yellow oil. CI Mass Spec: 179 (M+H).

Provenance & Evidence