3-Methylnaphthalene-2-carboxylic acid → (3-Methylnaphthalen-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methyl-2-naphthoic acid (5.0 g, 26.9 mmol) in anhydrous THF (75 mL) was cooled to 0° C. and treated with lithium aluminum hydride (1M in THF, 26.9 mL, 26.9 mmol) added dropwise. After the addition was complete, the resulting mixture was stirred 5 minutes at 0° C., the ice bath was removed, the mixture warmed to room temperature and stirred a total of 20 hours. The mixture was cooled to 0° C. and quenched by dropwise addition of water (1.02 mL), followed by 15% NaOH (1.02 mL), and more water (3 mL). The resulting mixture was stirred 1 hour and the granular precipitate removed by filtration through a plug of Florosil and anhydrous magnesium sulfate. The filtrate was concentrated in vacuo, to give the desired product (4.6 g, 99%) as a white crystalline solid of sufficient purity for use in the subsequent reaction.

Provenance & Evidence