Hydrochloric Acid → 4-Methoxy-α-methyl-β-oxobenzenepropanal

Participants

Reaction Steps

10 g (60.9 mmol) of 4′-methoxypropiophenone was dissolved in 100 ml of methyl formate. At room temperature, sodium methoxide, 15.3 g (79.2 mmol) at a concentration of 28% in methanol solution was dropwise added to the solution over a period of 30 minutes, followed by stirring at the same temperature for 6 hours. To the reaction mixture was added 100 ml of water, and the solution pH was adjusted to 1 with concentrated hydrochloric acid, followed by stirring for further 1 hour. Thereafter, the reaction mixture was extracted with 100 ml of ethyl acetate three times. The organic phase was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. Filtration and subsequent distillation to remove the solvent gave 9.8 g (51.0 mmol) of 2-formyl-4′-methoxypropiophenone as a light yellow crystal. The yield was 84%. The product synthesized was subjected to the next reaction without purification.

Provenance & Evidence