Hydrochloric Acid → 3-(2-Hydroxymethyl-5-nitrophenylthio)-4-hydroxybenzoic acid

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Reaction Steps

A mixture of 2-mercapto-4-nitrobenzyl alcohol (3.49 g, 18.86 mmoles), 4-hydroxy-3-iodo-benzoic acid (4.67 g, 17.69 mmoles), red cuprous oxide (1.35 g, 9.44 mmoles) and 1-methyl-2-pyrrolidinone (40 ml) was heated under a N2 atmosphere. The mixture became a thick slurry at about 90° but at 130° had become a dark red solution. After 1/2 hour at 140° TLC showed that the reaction was finished. The mixture was poured onto 2N HCl (200 ml) and after stirring for a few minutes it was extracted 4× with EtOAc. The EtOAc extracts were washed with water, then extracted 4× with 1N NaOH. The aqueous extracts were washed once with EtOAc then acidified and the resulting solid filtered, washed with water and dried to yield 4.65 g of the title compound.

Provenance & Evidence