METHYL 3-METHOXY-4-METHYLBENZOATE

Preparation

Methyl 3-methoxy-4-methylbenzoate is synthesized by the following steps:A mixture of methyl 3-hydroxy-4-methylbenzoate 36 (25 g, 0.151 mol),  Me2SO4 (28.3 ml, 0.386 mol), anhydrous K2CO3 (103.5 g, 0.75 mol) was  refluxed in acetone for 2 hours. K2CO3 was filtered off, washed  thoroughly with acetone. The filtrates were combined and concentrated,  the residue was redissolved in EtOAc washed with water, dried  (anhydrous Na2SO4), filtered and concentrated in vacuo to furnish a white solid (19.52 g).  Yield : 72%.

Chemical Properties

White low melting solid

Uses

Methyl 3-Methoxy-4-methylbenzoate has been used as a reactant in the preparation of an antimalaria drug that consists of the 4-aminoquinoline pharmacophore of chloroquine with clotrimazole-based antimalarials.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 33, p. 1771, 1990 DOI: 10.1021/jm00168a036

General Description

Methyl 3-methoxy-4-methylbenzoate can be prepared by reacting diazomethane with 3-methoxy-4-methylbenzoic acid in ether.