Hydrochloric Acid → 4-ALLYLSULFANYL-PHENOL

Participants

Reaction Steps

To a stirred solution of 4-hydroxythiophenol (1.6) (4.30 g, 34.1 mmol) in DMF (25 mL) were added K2CO3 (4.71 g, 34.1 mmol) and allyl bromide (3.09 mL, 34.1 mmol) at ice-water temperature, and the mixture was stirred for 15 minutes, prior to stirring overnight at room temperature. After the addition of 1 M aqueous HCl, the mixture was extracted with ether (3×). The combined organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10 to 1/6) to give 1.7 (5.74 g, 70%) as a white semi-solid. The 1H and 13C NMR spectra and mass spectrum were identical to the reported values (Tetrahedron 1994, 50, 10321-10330).

Provenance & Evidence