Ethylparaben → Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

Participants

Reaction Steps

Ethyl 4-hydroxybenzoate (50.0 g), methallyl chloride (32.6 g), and potassium carbonate (45.6 g) were refluxed in acetone (150 ml) with stirring for 40 hours. The reaction mixture was filtered and the filtrate was concentrated under a vacuum. The residue, with toluene (150 ml) added thereto, was washed with 2% sodium hydroxide solution and water successively. After being dried over sodium sulfate anhydride, the solution was concentrated under a vacuum. The resulting oily material was dissolved in N,N-dimethylaniline (80 ml) and refluxed with stirring for about 10 hours. The reaction mixture was acidified with concentrated hydrochloric acid while being cooled with ice and then extracted with toluene. The extract was further extracted with 10% aqueous sodium hydroxide solution. The resulting water layer was acidified with concentrated hydrochloric acid and then extracted with toluene. The extract was washed with water, dried over sodium sulfate anhydride, and then concentrated under a vacuum, thereby yielding 59.2 g of the aimed compound.

Provenance & Evidence