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 was 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, 3H), 6.88 (d, J=8.6 Hz, 2H), 7.65 (d, J=8.7 Hz, 2H), 7.74 (d, J=8.2 Hz, 2H), 8.07 (d, J=8.2 Hz, 2H), 10.51 (s, 1H).

Provenance & Evidence