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

Temperature

0 °C

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.

1. additionadded dropwise
2. additionAfter the addition
3. customthe ice bath was removed
4. temperaturethe mixture warmed to room temperature
5. stirringstirred a total of 20 hours
6. temperatureThe mixture was cooled to 0° C.
7. customquenched by dropwise addition of water (1.02 mL)
8. stirringThe resulting mixture was stirred 1 hour
9. customthe granular precipitate removed by filtration through a plug of Florosil and anhydrous magnesium sulfate
10. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-5d0a018efdcd4f4b87bd50640dfa4d04

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897405