Dimethyl Disulfide → 3-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A five liter flask equipped with a mechanical stirrer was charged with 100 g of 3-bromo-4-hydroxy-5-benzyloxybenzaldehyde, 80 g Cu powder, 80 mL methyldisulfide and 1.7 L pyridine, and the mixture was heated at 90° C. overnight with gentle stirring. The following day, the reaction mixture was filtered and most of the pyridine (1.3 L) was distilled off. The remaining solid residue was washed with about 2 L of methylene chloride and combined with the residue left after pyridine evaporation. The combined organic fraction was washed with 1.5 N HCl until the dark methylene chloride layer turned light brown and the aqueous layer was clear. The resulting light brown methylene chloride layer was dried over MgSO4 and filtered through a bed of silica gel. Evaporation and crystallization from methylene chloride-hexane gave the title compound: NMR(200 MHz, CDCl3) 2.50(s, SCH3), 5.20(s, OCH2Ar), 6.72(s, OH), 7.34-7.46(m, ArH), 9.78(s, ArCHO).

Provenance & Evidence