Methyl iodide → HCID 13853500, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (380 mg. 50% oil) was added portionwise to a solution of diethyl 3-methyl-5-hydroxyphthalate (2 gm) in dry tetrahydrofuran (50 ml). The solution was stirred for 30 minutes. Methyl iodide (2 ml), tetra-n-butylammonium iodide (45 mg) and HMPA (5 ml) was added. The solution was stirred at room temperature for 21/2 hours at refluxed at 60° C. for 1 hour. The solvent was removed under reduced pressure. The oil was partitioned between ethyl acetate and 5% hydrochloric acid solution. The ethyl acetate layer was washed with brine solution and dried over magnesium sulphate. Solvent evaporation gave an oil which was chromatographed (20% ethyl acetate:petroleum ether) to give diethyl 3-methyl-5-methoxy-phthalate.

Provenance & Evidence