Synthesis of 2-(naphthalen-1-yl)propan-1-ol

Preparation of 2-(naphthalen-1-yl)propan-1-ol (2-(1-naphthyl)-1-propanol)

Preparation of 2-(naphthalen-1-yl)propan-1-ol (2-(1-naphthyl)-1-propanol)

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).

IUPAC Name

2-naphthalen-1-ylpropan-1-ol

InChI

InChI=1S/C13H14O/c1-10(9-14)12-8-4-6-11-5-2-3-7-13(11)12/h2-8,10,14H,9H2,1H3

InChI Key

YZMWRFOKAISJQX-UHFFFAOYSA-N

Canonical SMILES

CC(CO)C1=CC=CC2=CC=CC=C21

Depositor-Supplied Synonyms

SCHEMBL3412393, AKOS014312086

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