13807-91-5

1-Benzyloxy-2-propanol is an intermediate used in the synthetic preparation of glucokinase activators for the treatment of diabetes.

A first mixture was obtained by adding 11 g of benzyl alcohol (0.1 mol) together with 11.4 g of potassium tert-butoxide (as the first catalyst, 0.1 mol) to 150 mL of anhydrous tetrahydrofuran (THF) at 0 °C with continuous stirring for 30 min. Subsequently, propylene oxide was slowly added dropwise to the first mixture at 0 °C for a ring-opening reaction with continuous stirring for 24 hours. The molar ratio of benzyl alcohol, propylene oxide to the first catalyst in the reaction system was 1:1:1. Upon completion of the reaction, the pH of the reaction system was adjusted to 7 using 30 wt% dilute aqueous acetic acid. after removal of THF by rotary evaporation, 300 mL of ethyl acetate was added for extraction. The organic phase was washed three times with 100 mL of water and subsequently dried with 25 g of anhydrous sodium sulfate for 3 hr. After filtration to remove the desiccant, the organic phase was concentrated and purified by column chromatography (eluent ratio ethyl acetate:n-heptane=1:5) to give 13.8 g of a colorless oily substance (the target product 1-(benzyloxy)propan-2-ol) in 90% yield by weight.

[1] Patent: CN108276355, 2018, A. Location in patent: Paragraph 0110; 0111; 0112; 0113
[2] Journal of the American Chemical Society, 2006, vol. 128, # 16, p. 5360 - 5361
[3] Applied Catalysis A: General, 2011, vol. 408, # 1-2, p. 125 - 129