Iodine → (2-([2-(Hydroxymethyl)phenyl]disulfanyl)phenyl)methanol

Participants

Reaction Steps

A solution of 30.8 g (0.20 mol) of o-mercaptobenzoic acid in 300 ml of dioxane was added to a mixture of 15.2 g (0.40 mol) lithium aluminum hydride in 300 ml of dioxane. 160 ml of tetrahydrofuran ("THF") was slowly added to this mixture with some loss of material due to bumping. The mixture was stirred for 2 hours followed by the slow addition of 15.2 ml of water, then 15.2 ml of 15% NaOH and finally 45.6 ml of water. The mixture was filtered with a methanol wash and the filtrate was concentrated to 20.0 g of oil. Methanol (250 ml) and 18.1 g (0.07 mol) of iodine were added and the mixture was stirred over the weekend. An equal volume of saturated NaCl solution was added and the solid was collected, washed with water, and recrystallized from aqueous ethanol. The yield of bis(2-hydroxymethylphenyl) disulfide was 10.0 g and had amp of 138.5°-139.5° C.

Provenance & Evidence