Hydrochloric Acid → HCID 88184493, compound

Participants

Reaction Steps

Methanethiol sodium salt (4.0 g, 52 mmol) was added to a solution (70 mL) of 2-bromobenzaldehyde (9.25 g, 50 mmol) in N,N-dimethylformamide, followed by reflux for 2 hours. Next, the reaction solution was added to dilute hydrochloric acid (0.5 mol/L) under ice-cooling to neutralize the reaction solution, and the mixture was then extracted with ethyl acetate. After the extract was washed with a saturated aqueous solution of sodium bicarbonate and with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained crude 2-methylthiobenzaldehyde was dissolved in ethyl acetate (30 mL), and methyl triphenylphosphoranylideneacetate (16.7 g, 50 mmol) was added thereto, followed by stirring at room temperature for 12 hours. Thereafter, the solvent was evaporated under reduced pressure, and the residue was powdered with hexane to give methyl o-methylthiocinnamate (5.43 g, yield 51%).

Provenance & Evidence