Propargyl alcohol → 2-(Phenylsulfanyl)prop-2-en-1-ol

To a stirred solution of 36.0 g (0.64 mol) of propargyl alcohol and 0.12 g (1.8 mmol) of powdered potassium hydroxide, was added dropwise at 125° C. over 30 minutes, 60.0 g (0.54 mol) of thiophenol. The mixture was stirred for an additional 90 minutes, and allowed to cool to room temperature. The brown solution was diluted with 200 mL of ether, and extracted with three 100-mL portions of 2N sodium hydroxide, and two 100-mL portions of water. The organic phase was dried over MgSO4, filtered, and the solvent removed in vacuo from a water bath at 45° C. to give 90.4 g of a brown liquid, which, according to NMR analysis, contained 34% of the desired isomer. The mixture was fractionally distilled through a 0.8×20-cm column packed with glass helices to give 29.5 g of a colorless liquid, which by NMR analysis contained 67% of the desired isomer, bp 109°-116° C./1.2 Torr. This liquid was chromatographed on silica gel (100-200 mesh, 50 g/gram of compound) with 20% EtOAc/Skelly B as eluant, to give 16.4 g (18%) of the sulfide as a colorless liquid; IR (neat) cm-1 3360, 1610, 1580, 1470, 1430, 1040, 740, 690; 1H NMR (CDCl3) δ3.70 (t, 1H, OH), 4.10 (d, 2H, CH2), 5.2 (t, J=1 Hz, 1H, vinyl), 5.55 (t, J=1 Hz, 1H, vinyl), 7.15-7.55 (m, 5H, phenyl).

1. extractionextracted with three 100-mL portions of 2N sodium hydroxide, and two 100-mL portions of water
2. dry with materialThe organic phase was dried over MgSO4
3. filtrationfiltered
4. customthe solvent removed in vacuo from a water bath at 45° C.

ORD record

ord-2d224b0de8af4162b420451a2ea401ce

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05221754