反应详情

A mixture of 2,4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol), sodium acetate (5.94 g, 72.4 mmol), nitroethane (5.44 g, 72.4 mmol) and glacial acetic acid (10 ml) was refluxed for 6 hours. After cooling, the mixture was poured onto ice (100 g) and extracted with ethyl acetate (4×50 ml). The combined organic layers were washed with saturated NaHCO3 until the pK of the aqueous layer remained at 8, dried (Na2SO4) and the solvent removed in vacuo. Flash chromatography (SiO2, cyclohexane: ethyl acetate=1:1) afforded 2,4-dihydroxybenzonitrile (2.87 g, 59%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ6.33 (d, 1 H, J=8.6 Hz), 6.43 (s, 1 H), 7.37 (d, 1 H, J=8.6 Hz), 10.35 (s, 1 H), 10.78 (s, 1 H). IR (KBr) 2200 cm−1.

1. temperaturewas refluxed for 6 hours
2. temperatureAfter cooling
3. additionthe mixture was poured onto ice (100 g)
4. extractionextracted with ethyl acetate (4×50 ml)
5. washThe combined organic layers were washed with saturated NaHCO3 until the pK of the aqueous layer
6. dry with materialdried (Na2SO4)
7. customthe solvent removed in vacuo