Hydrochloric Acid → 4-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanal

Participants

Reaction Steps

To a solution of 82.65 g (66.29 g, 0.2177 mol) of 4cyclohexyl-3-methyl-4-oxo-3-phenylbutyraldehyde dimethyl acetal in 539 mL of acetone was added 539 mL of 3 N HCl (aq) at RT. After reaction completion (2 h), the mixture was concentrated to 426.5 g (or ⅓ volume) of residue (RT−40° C.). The residue contained mostly water (pH=0) and was extracted twice with 300 mL of MTBE. The MTBE extract was washed with 300 mL of 25% NaCl (aq), dried over MgSO4, gravity filtered and concentrated to afford 54.92 g (97.65%) of title compound as a pink oil: 1H NMR (d6-DMSO): δ 9.54 (t, J=2.0 Hz, 1H, —CHO), 7.36-7.45 (m, 2H, phenyl CH), 7.28-7.35 (m, 3H, phenyl CH), 2.95 (dd, J=16.6 Hz, J=1.9 Hz, 1H, CH2CHO), 2.85 (dd, J=16.6 Hz, J=1.7 Hz, 1H, CH2CHO), 2.41-2.49 (m, 1H, cyclohexyl CH), 1.72 (s, 3H, R2C(CH3)Ph), 0.85-1.66 (m, 10H, cyclohexyl —CH2).

Provenance & Evidence