4-Formylbenzoic acid → 4-[3-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid

Participants

Reaction Steps

To a solution of 78.7 mg (0.272 mmol) 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene (Compound 100G) in 4.0 ml of MeOH was added 53.1 mg (0.354 mmol) of 4-carboxy benzaldehyde, and 80 mg (2.00 mmol; 2.0 ml of 1M aqueous NaOH). The resulting solution was stirred at room temperature for 12 hours, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer was washed with H2O, and saturated aqueous NaCl, then dried over Na2SO4. Removal of the solvents under reduced pressure gave the title compound as a colorless solid which was purified by recrystallization from CH3CN. 1H NMR (acetone-d6): δ 8.00 (7H, m), 7.83 (1H, d, J=15.6 Hz), 7.24 (4H, s), 7.13 (1H, d, J=8.1 Hz), 6.12 (1H, t, J=4.5 Hz), 2.42 (2H, d, J=4.8 Hz), 2.38 (3H, s), 1.41 (6H, s).

Provenance & Evidence