4-Hydroxybenzaldehyde → HCID 243062, compound

Participants

Reaction Steps

4-hydroxybenzaldehyde (30 g), ethyl cyanoacetate (31.7 g), acetic acid (4.5 ml) and ammonium acetate (1.9 g) were refluxed in ethyl alcohol (100 ml) for 4 hours with heating. After the reaction, the reacting solution was poured into 500 ml of ice-cold water to separate crystals. The resulting crystals were recrystallized from methyl alcohol (400 ml) to obtain 65 g of ethyl-2-cyano-3-(4-hydroxyphenyl)acrylate which melted at 89°-91° C. The resulting compound (10.9 g) and pyridine (4.3 g) were dissolved in tetrahydrofuran (100 ml), and acryloyl chloride (4.5 g) was added dropwise thereto. The reaction was carried out for 2 hours while keeping the reaction temperature below 40° C. After the reaction, the reacting solution was poured into ice-cold water to separate crystals, and the resulting crystals were recrystallized from methyl alcohol (100 ml) to obtain 11 g of the desired product which melted at 82°-85° C. The resulting compound was confirmed by the results of IR, NMR and elementary analysis.

Provenance & Evidence