Benzoic acid, 4-(4-methoxybenzoyl)-, methyl ester → Methyl 4-(4-hydroxybenzoyl)benzoate

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Reaction Steps

To a 3-necked round-bottomed flask was added AlCl3 (32 g, 0.24 mol.) followed by anhydrous toluene (250 mL). The flask was equipped with a reflux condenser and nitrogen inlet and the suspension was stirred at RT under a nitrogen atmosphere. To the stirred suspension was added methyl 4-{[4-(methyloxy)phenyl]carbonyl}benzoate (23) (16.0 g, 0.059 mol.) portionwise at RT under a nitrogen atmosphere. The reaction mixture was heated at 85° C. with stirring under a nitrogen atmosphere. After 2 h, the oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was cooled in an ice-water bath and ice was added very slowly portionwise (Note: significant HCl evolved upon addition of ice to the reaction mixture.) followed by the slow addition of ice-water. The reaction mixture was partitioned between EtOAc and water. The organic phase washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the crude product as a red-brown solid. The crude product was triturated with hot hexanes and the brown solid was filtered to give 14.0 g (93%) of compound 24. 1H NMR (400 MHz, DMSO-d6): δ 3.88 (s, 3 H), 6.88 (d, J=8.6 Hz, 2 H), 7.65 (d, J=8.7 Hz, 2 H), 7.74 (d, J=8.2 Hz, 2 H), 8.07 (d, J=8.2 Hz, 2 H), 10.51 (s, 1 H).

Provenance & Evidence