Methyl iodide → DL-2-(4-chlorophenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, to a mixture of (4-chlorophenyl)acetic acid (13.6 g) in THF (140 mL) was added n-butyllithium (1.6 M hexane solution, 100 mL) at −60° C. to −70° C., and the mixture was allowed to warm to 0° C. A mixture of methyl iodide (4.96 mL) in THF (40 mL) was added to the reaction mixture at 0° C.-10° C., and the mixture was stirred at room temperature for 12 hr. The reaction mixture was extracted with 1N aqueous sodium hydroxide solution (2×100 mL), and the extract was acidified with 3N hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate (3×100 mL), the extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.3 g).

Provenance & Evidence