Preparation of 2-(naphthalen-1-yl)propan-1-ol (2-(1-naphthyl)-1-propanol)
A mixture of 83.5 g of 2-(1-naphthyl)propionaldehyde, 300 ml of acetic acid, 300 ml of water, and 200 g of iron powder is heated for 7 hours on the steam-bath. The solution is then filtered and the filter-cake is washed with water and then with ether. The filtrate and wash-water are diluted with water and then extracted with ether. The oil remaining after evaporation of the ether is boiled with a solution of 15 g of NaOH in 30 ml of water and 50 ml of alcohol to cleave the acetate that has been formed. The alcohol is then washed, dried in ethereal solution, and distilled. 2-(Naphthalen-1-yl)propan-1-ol is obtained as a yellowish viscous oil of b.p. 144-147°/3 mm, in 78.5% yield (66.3 g).
J. Amer. Chem. Soc, 61, 2137 (1939).