2-[(4-ethenylphenyl)methylsulfanyl]ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 152 g (1.0 mole) of p-(chloromethyl)styrene, 60 g (1.5 moles) of sodium hydroxide and 0.5 liter of tetrahydrofuran. The resulting mixture was boiled, and 78 g (1.0 mole) of 2-mercaptoethanol was added dropwise over 0.5 hour. The boiling was continued for 3 hours. After cooling to room temperature, the reaction mixture was filtered by the same operation as in Example 1, and distilled under reduced pressure (140-145 ° C./1-2 mmHg) to give 93 g of 2-(4-vinylbenzylthio)ethanol as a white solid. the reaction mixture was filtered by the same operation as in Example 1 distilled under reduced pressure (140-145 ° C./1-2 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°45.5° C. Yield of 85%. Analysis calculated for C11H 14 OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 152 g (1.0 mole) of p-(chloromethyl)styrene, 60 g (1.5 moles) of sodium hydroxide and 0.5 liter of tetrahydrofuran. The resulting mixture was boiled, and 78 g (1.0 mole) of 2-mercaptoethanol was added dropwise over 0.5 hour. The boiling was continued for 3 hours. After cooling to room temperature, the reaction mixture was filtered by the same operation as in Example 1, and distilled under reduced pressure (140-145 ° C./1-2 mmHg) to give 93 g of 2-(4-vinylbenzylthio)ethanol as a white solid. the reaction mixture was filtered by the same operation as in Example 1 distilled under reduced pressure (140-145 ° C./1-2 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37. over fifteen minutes addition the solution After addition The mixture was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the solvent was washed with water (3×200 ml) with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate filtered the solvent removed on a rotary evaporator To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml) The product crystallized was then filtered to give a white solid