Benzaldehyde → HCID 2760079, compound

Participants

Reaction Steps

A solution of 4-bromophenyl methyl sulfide (Aldrich) (3.3 g, 16.4 mmol) in 10 mL of dry diethyl ether is slowly added to a stirred suspension of magnesium turnings (0.44 g, 18.1 mmol) and three crystals of iodine in 10 mL of boiling dry diethyl ether. The reaction is heated at reflux for several hours until almost all the magnesium is consumed. The reaction is cooled to room temperature, and a solution of benzaldehyde (2.0 mL, 19.7 mmol) in 50 mL of dry diethyl ether is added dropwise. The reaction mixture is diluted with ethyl acetate and washed twice with 1N HCl, followed by saturated aqueous sodium bicarbonate, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude solid is crystallized from diethyl ether/hexane to give 2.4 g (64%) of 4-methylthiobenzhydrol: melting point 92°-93.5° C.

Provenance & Evidence