Hydrochloric Acid → 1-(1-Naphthyl)ethanol

Participants

Reaction Steps

To a solution of methylmagnesium iodide in ether which was prepared from magnesium turning (1.08 g, 44.4 mmol) and methyl iodide (2.75 ml, 44.2 mmol) in 100 ml of ether, were added a solution of 1-naphthaldehyde (1) (5.75 g, 36.8 mmol) in 10 ml of ether with cooling in an ice-water bath, then the resulting reaction mixture was stirred for 2 hours at room temperature. To this mixture was added 25 ml of 2N hydrochloric acid and then the organic layer was separated from the aqueous layer. The organic layer was washed with 50 ml of brine and dried over sodium sulfate. Evaporation of the solvent in vacuo gave 6.20 g (97%) of 2 as a viscous oil.

Provenance & Evidence