Hydrochloric Acid → 4'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehyde

Participants

Reaction Steps

A solution of 4′-hydroxy-3-methyl[1,1′-biphenyl]-4-carbonitrile (500 mg, 2.39 mmol) in dry toluene was cooled to −78° C. and diisobutylaluminum hydride (4.0 mL of 1.5 M solution in toluene, 5.98 mmol) was added all at once. The reaction mixture was allowed to warm to room temperature over a period of 3.5 h. Methanol (1.2 mL) was added followed by water (1.2 mL) at 0° C. and the mixture was stirred at room temperature for 20 min. 1 N HCl solution was added with stirring until pH<7. The mixture was extracted with ethyl acetate (3×), washed with brine, dried over sodium sulfate, filtered, and the solvent evaporated. Purification by silica chromatography (15%-25% ethyl acetate-hexane) to yield 459 mg (91%) of the title compound as a white solid: mp 161-162° C.; 1H NMR (DMSO-d6): δ 2.67 (3H, s), 6.88 (2H, d, J=8.41 Hz), 7.59-7.65 (4H, m), 7.85 (1H,d, J=8.03 Hz), 9.78 (1H, s), 10.22 (1H, s); IR 1680 cm−1; MS (ESI) m/z 211 (M−H)−.

Provenance & Evidence