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0 °C

14.6 g of sodium hydride (60 % in oil) was washed with n-pentane under an argon gas. After drying, 150 ml of dry dimethylformamide (hereinafter referred to simply as DMF) was added thereto to form a suspension. 75 g of (Z)-2-buten-1,4-diol was dropwise added thereto at 0° C. under stirring over a period of 30 minutes. The mixture was stirred at room temperature for 1.5 hours, and 44 g of benzyl bromide was added at 0° C. under stirring. The mixture was stirred at the same temperature for 30 minutes, and then the temperature was returned to room temperature. The mixture was stirred at 50° C. overnight. The reaction solution was poured into ice water and extracted with diethyl ether. The ether solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.5 mmHg, 134°-138° C.) to obtain 29 g of (Z)-4-benzyloxy-2-buten-1-ol as colorless oily substance.

1. wash14.6 g of sodium hydride (60 % in oil) was washed with n-pentane under an argon gas
2. customAfter drying
3. additionwas added
4. customto form a suspension
5. stirringThe mixture was stirred at room temperature for 1.5 hours
6. stirringunder stirring
7. stirringThe mixture was stirred at the same temperature for 30 minutes
8. customwas returned to room temperature
9. stirringThe mixture was stirred at 50° C. overnight
10. extractionextracted with diethyl ether
11. washThe ether solution was washed sequentially with water and with a saturated sodium chloride aqueous solution
12. dry with materialdried over anhydrous magnesium sulfate
13. distillationThe solvent was distilled off under reduced pressure
14. distillationthe residue was subjected to distillation under reduced pressure (2.5 mmHg, 134°-138° C.)