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

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Reaction Steps

Ethyl 4-hydroxybenzoate (50.0 g), methallyl chloride (32.6 g) and potassium carbonate (45.6 g) were refluxed with heating in acetone (150 ml) for 40 hours. The reaction mixture was filtrated and the filtrate was concentrated under a vacuum. The residue, after toluene (150 ml) was added thereto, was washed with 2% sodium hydroxide aqueous solution and water successively. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum, thereby yielding an oily compound. This compound was dissolved in N,N-dimethylaniline (80 ml) and refluxed with heating for about 10 hours. While being cooled with ice, the reaction mixture was acidified with concentrated hydrochloric acid and then extracted with toluene. The extract was extracted with 10% sodium hydroxide aqueous solution. The 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 ethyl 4-hydroxy-3-methallylbenzoate.

Provenance & Evidence