Hydrochloric Acid → 3-(p-Vinylbenzylthio)propionic acid

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Reaction Steps

To a solution of potassium hydroxide (84 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1.2 liter) at room temperature was added under a nitrogen atmosphere 3-mercaptopropionic acid (65.0 g, 0.61 mole) over 10 minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (93 g. 0.6 mole) was added at room temperature over 30 minutes. After addition, the solution was stirred at ambient temperature overnight. The next day the mixture was poured into ice and concentrated hydrochloric acid (150 ml). The solid was filtered and dried on a funnel under vacuum. The solid was dissolved in dichloromethane (1.4 liter), washed with saturated NaCl (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. The residue was dissolved in diethyl ether (600 ml), hexane (1 liter) was added to the cloud point, and then the mixture was placed in a freezer. The white solid product was collected by filtration: m.p. of 77°-78° C. Yield of 80%. Analysis calculated for C12H14O2S: C, 64.84, H, 6.35, S, 14.42. Found: C, 64.98, H, 6.29, S, 14.02. 1H NMR (CDCl3) δ 2.6 (m, 4H, CH2CH2), 3.7 (s, 2H, ArCH2S), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.65 (m, 1H, CH=), 7.3 (m, 4H, ArH's).

Provenance & Evidence