Methanol → (5-Methyl-2-nitrophenyl)methanol

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Reaction Steps

60 ml of borane-dimethyl sulphide complex are added over the course of 30 minutes to a boiling solution of 100 g of 5-methyl-2-nitrobenzoic acid in 750 ml of tetrahydrofuran. The reaction solution is boiled for 4 hours under reflux conditions. Then, 200 ml of methanol are added with cooling, and the solution is left to stand for 30 minutes at room temperature. It is then evaporated in a vacuum until dry and the residue thus obtained is partitioned between chloroform and sodium carbonate solution. The organic phase is washed with water, dried over sodium sulphate and evaporated, whereupon the heading compound is obtained as a crystalline solid having a low melting point.

Provenance & Evidence