2-Phenylethanol → Phenethyl tosylate

To a stirred solution of phenethyl alcohol (0.50 mL, 4.17 mmol) in pyridine (4 mL) at 0° C. was added p-toluenesulfonyl chloride (0.80 g, 4.18 mmol). The reaction mixture was stirred for 16 h, and then diluted with ethyl acetate (75 mL). The organic solution was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL), then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 0-20% ethyl acetate in hexane to afford the title compound as a light yellow liquid (0.59 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.69 (d, J=8.3 Hz, 2H), 7.31-7.20 (m, 5H), 7.11 (dd, J=7.4, 1.7 Hz, 2H), 4.21 (t, J=7.1 Hz, 2H), 2.96 (t, J=7.1 Hz, 2H), 2.43 (s, 3H); MS (ES+) m/z 299.2 (M+23).

1. washThe organic solution was washed with 10% aqueous hydrochloric acid (2×25 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo
5. customthe residue was purified by column chromatography
6. washeluting with 0-20% ethyl acetate in hexane

ORD record

ord-1bc73511aca9494aa6bb9d051324f4d1

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501746B2