Hydrochloric Acid → Methyl (2-methylphenyl)(oxo)acetate

Participants

Reaction Steps

5.1 g of magnesium (0.21 mol) was placed in 300 ml of dry ether and 34.18 g of o-bromotoluene (0.2 mol) was added dropwise thereto under a nitrogen atmosphere to prepare a Grignard reagent. The Grignard reagent solution was cooled to −78° C. and 23.6 g of dimethyl oxalate (0.2 mol) was added dropwise thereto. The resulting solution was stirred for 30 minutes, mixed with crushed ice, acidified with 20% hydrochloric acid and then extracted with ether. The organic layer was washed three times with water, dried over magnesium sulfate, and the solvent was removed under a reduced pressure to obtain a residue. The residue was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (9:1) as an eluent to obtain 24.2 g (yield 68%) of the title compound as a colorless liquid.

Provenance & Evidence