Sodium Hydroxide → 3-(4-Methoxyphenyl)propane-1-thiol

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Reaction Steps

A mixture of 3-(4-methoxyphenyl)-1-propylbromide (14 g; 61 mmol) and thiourea (5.1 g; 67 mmol) in ethanol (150 mL) was refluxed for 48 hours. Evaporation of the solvent provided a clear glassy compound, which was dissolved in 50 mL of water and treated with 100 mL of 40% aqueous sodium hydroxide. After stirring the resulting mixture for two hours, the product was extracted into ether (3×), and the combined organic extracts were washed with sodium bicarbonate and brine, dried, and concentrated. Chromatographic purification of the crude thiol on a silica gel column eluting with 2% either in hexane delivered 10.2 g of 3-(4-methoxyphenyl)-1-propylmercaptan as a clear liquid 1H NMR (300 MHZ, CDCl3):δ 1.34 (t, 1H); 1.88-1.92 (m,2H); 2.49-2.53 (m,2H); 2.64-2.69 (m, 2H); 3.77 (s, 3H); 6.80-6.84 (m,2H); 7.06-7.24 (m,2H).

Provenance & Evidence