Tetrahydrofuran → 5-(Allyloxy)-2-sulfanylphenol

Participants

Reaction Steps

6-(Allyloxy)-1,3-benzoxathiol-2-one (48.3 g, 0.232 mol) was dissolved in aq. NaOH solution (2M, 300 ml) and THF (300 ml) to give a yellow solution which stirred at RT for 2 h. The THF was removed in vacuo, a small amount of precipitated starting material removed by filtration, and further starting material was removed by extraction of the aqueous phase into diethyl ether (3×300 ml). The aqueous phase was then acidified to pH 1 with cHCl (˜150 ml) with ice-cooling. Gas evolution was observed, and after 15 min, the title compound was obtained following extraction into diethyl ether (3×300 ml), drying over MgSO4 and concentration to a yellow oil (37.84 g, 0.18 mol).

Provenance & Evidence