3-Hydroxybenzaldehyde → HCID 58027707, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of t-BuO−K+ (68.5 g, 614 mmol) in THF, cooled to −50° C., was added acetonitrile (30.3 mL, 540 mmol), dropwise over a period of 5 min. The resulting mixture was stirred at −50° C. for 30 min following which a solution of 3-hydroxybenzaldehyde (21.2) (30.0 g, 244 mmol) in THF was added slowly, over a period of 10 min. This was then allowed to warm to 0° C. and stirred for another 3 h during which the reaction was complete. The reaction was quenched by slow addition of ice-water followed by extraction with EtOAc. The combined organics were washed with water, brine and dried over Na2SO4. The solution was concentrated under reduced pressure to give 3-hydroxy-3-(3-hydroxyphenyl)propanenitrile (21.16) as yellow oil which was purified by flash column chromatography (0 to 20% EtOAc—hexanes gradient). Yield (25.0 g, 62%); 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.90-6.93 (m, 1H), 6.82 (dd, J=8.0, 2.4 Hz, 1H), 4.91-5.03 (m, 1H), 2.76 (d, J=6.4 Hz, 2H).

Provenance & Evidence