Methanol → Methyl 3-(hydroxymethyl)-5-iodobenzoate

Participants

Reaction Steps

Methanol (20 ml) was added dropwise to a mixture of dimethyl 5-iodoisophthalate (20.0 g) and sodium borohydride (2.4 g) in tetrahydrofuran (200 ml) for 15 minutes at 45-50° C., and the mixture was stirred for 1 hour at same temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and the separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform-methanol (19:1, V/V) as an eluent. The fractions containing the desired product were collected and evaporated in vacuo to give methyl 5-hydroxymethyl-3-iodobenzoate (15.11 g).

Provenance & Evidence