4-Hydroxybenzaldehyde → 4-(1,3-dithian-2-yl)phenol

Participants

Reaction Conditions

Reaction Steps

4-Hydroxybenzaldehyde (46 g, 0.377 mol), recrystallized from benzene, and 1,3-propanedithiol (45 ml, 0.449 mol) were added to dry chloroform. The reaction mixture was stirred at 0° C. and HCl gas was bubbled through the solution for 10 minutes. After the exothermic reaction stopped the solution was refluxed for 10 hours. A white precipitate formed. This was filtered off and the chloroform solution was washed with water three times, dried (MgSo4) and evaporated under reduced pressure to yield a light yellow solid. White needles were obtained after recrystallization from chloroform, MP=151°-152° C. The white precipitate was also recrystallized from chloroform to yield white needles that melted at 151°-152° C. IR and NMR confirmed the two compounds to be identical. Total yield after recrystallization: 99%.

Provenance & Evidence