1-phenylmethoxybutan-2-ol

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

Procedure: To a solution of 1,000 g. (5.45 mole) of 1-benzyloxy-2-butanol in 2,000 ml. of pyridine, 1,170 g. (6.04 mole) of p-toluenesulfonyl chloride is added in small portions for a period of about 30 minutes at room temperature. During the addition the temperature raises, but it is kept at the room values by cooling the reaction mixture by an external circulation of ice-water; then the solution is vigorously stirred always at room temperature for about 16-20 hours. After cooling to 0°C, the solution is poured into ice-water and an oil precipitates, which is separated from the aqueous phase by decantation. The remaining water portion is twice extracted with benzene; then the oily and the benzene phases are combined together and the resulting benzene solution is cooled to about 10°C. Said organic solution is subsequently washed with concentrated hydrochloric acid, then with a saturated solution of sodium bicarbonate and finally with water, and dried over sodium sulfate. After distillation of the solvent a residue is obtained which is 1-benzyloxy-2-butanol p-toluenesulfonate which decomposes upon distillation. Yield of this step: 100%. During the addition the temperature raises After cooling to 0°C an oil precipitates which is separated from the aqueous phase by decantation The remaining water portion is twice extracted with benzene the resulting benzene solution is cooled to about 10°C is subsequently washed with concentrated hydrochloric acid with a saturated solution of sodium bicarbonate and finally with water, and dried over sodium sulfate After distillation of the solvent a residue is obtained which decomposes upon distillation

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

Procedure: 15.4 Grams (0.67 mole) of sodium are poured into a flask containing 3.500 g. (35.2 mole) of benzyl alcohol under nitrogen atmosphere. After the sodium is dissolved, the temperature is brought to 160°C, then 481 g. (6.7 mole) of 1,2-epoxybutane are added dropwise. The temperature is kept at 160°C during the approximately 2 hours addition period. The temperature is subsequently lowered to 120°C and the excess of the starting 1,2-epoxybutane is distilled off; then 33.8 g (0.335 mole) of concentrated sulfuric acid and 36 ml. of water are added to the reaction mixture and the resulting solid sodium sulfate is removed by filtration. The filtrate is distilled under reduced pressure, thus recovering pure 1-benzyloxy-2-butanol in a yield of 90%. B.p. 128-132/6 mmHg. containing 3.500 g is brought to 160°C The temperature is kept at 160°C during the approximately 2 hours addition period is subsequently lowered to 120°C the excess of the starting 1,2-epoxybutane is distilled off the resulting solid sodium sulfate is removed by filtration The filtrate is distilled under reduced pressure thus recovering pure 1-benzyloxy-2-butanol in a yield of 90%