Methyl iodide → 2-(Naphthalen-1-yl)propanoic acid

HRID 1683159Notes

Reaction equation

[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:15]([Li])CCC.IC>C1COCC1>[C:1]1([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -10 °C

Procedure

1-Naphthylacetic acid (10 g, 53.7 mmol) is dissolved in dry THF (150 mL) under nitrogen. The solution is cooled to -10° C., treated with 1.6M butyl lithium in hexanes (72 mL, 115 mmol), and stirred for 15 minutes. A solution of iodomethane (3.7 mL, 59.4 mmol) in dry THF (50 mL) is added, and the mixture is allowed to warm to room temperature and stir for several hours. The solvent is removed in vacuo, and the residue dissolved in 5% sodium hydroxide solution (500 mL), washed with ether (3×200 mL), and then acidified by the addition of 6N hydrochloric acid. The aqueous is then extracted with dichloromethane (3×200 mL), the organic extracts are dried over sodium sulfate, and the solvent removed to leave 2-(1-naphthyl)propionic acid as a white solid.

Workup

temperatureto warm to room temperature
stirringstir for several hours
customThe solvent is removed in vacuo
dissolutionthe residue dissolved in 5% sodium hydroxide solution (500 mL)
washwashed with ether (3×200 mL)
additionacidified by the addition of 6N hydrochloric acid
extractionThe aqueous is then extracted with dichloromethane (3×200 mL)
dry with materialthe organic extracts are dried over sodium sulfate
customthe solvent removed

Sources & evidence

ORD record: ord-ab1bbf48d2bf490d9050f5385727cb09
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637583

Reaction notes

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