4-Hydroxybenzaldehyde → Methyl 5-(4-hydroxyphenyl)-3-oxo-4-pentenoate

Participants

Reaction Steps

##STR7## 232 g (2 mol) of methyl acetoacetate, 244 g (2 mol) of 4-hydroxybenzaldehyde, 24 g (0.4 mol) of glacial acetic acid and 6.8 g (0.08 mol) of piperidine were dissolved in 459 ml of methylcyclohexane. The reaction solution was heated to the boil, and the water of reaction was separated off for one hour in a water separator. After the solvent had been decanted, the product was taken up in diethyl ether, filtered off with suction and dried. 362 g (corresponding to a yield of 82%) of methyl 4-hydroxybenzalacetoacetate were obtained. 22 g (0.1 mol) of methyl 4-hydroxybenzalacetoacetate were dissolved in 100 ml of methanol, and 5.6 g (0.1 mol) of KOH in 38 g of methanol were added. Stirring was carried out for 2.5 hours at room temperature, after which the reaction mixture was evaporated down and the remaining residue was dried. 25 g (corresponding to a yield of 97% of the title compound were obtained in the form of a red solid. The purity of the product was >95%.

Provenance & Evidence