Carbon Dioxide → HCID 54010142, compound

Participants

Reaction Conditions

Reaction Steps

A 100 ml. round bottom flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet and bubbler, and a heated oil bath was charged with 14.9 g. of crude α-cyano-3-hydroxy-4-methoxydihydrocinnamic acid (above) and freshly redistilled quinoline (8 ml.). The acid underwent smooth decarboxylation at an oil bath temperature of 150°-155°C with CO2 evolution continuing 45 min. The mixture was then heated 1 hour at 165°C (oil bath) and permitted to cool to room temperature. For workup, the cooled mixture was treated with 500 ml. of 1N HCl and extracted thoroughly with several portions of ether totalling 350 ml. The ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.), and finally dried over anhydrous Na2SO4. Concentration of the ether solution gave 8.3 g. (70% yield) of β-(3-hydroxy-4-methoxyphenyl)propionitrile as a pale yellow solid. Recrystallization from ethyl acetate/hexane gave the pure compound as light yellow crystals, m.p. 82°C (62% yield of recrystallized product).

Provenance & Evidence