Hydrochloric Acid → Benzoic acid, 4-(4-methoxybenzoyl)-, methyl ester

Participants

Reaction Steps

To a 3-necked round-bottomed flask equipped with a magnetic stir bar were added anisole (31 mL, 30.8 g, 0.285 moL) and terephthalic acid monomethyl ester chloride (19.6 g, 0.099 moL). The flask was equipped with a powder addition funnel and nitrogen inlet. The powder addition funnel was charged with AlCl3 (40.2 g, 0.301 moL). The reaction mixture was cooled in an ice-water bath and the AlCl3 was added slowly, portionwise with stirring, under a nitrogen atmosphere. The ice-water bath was removed and the stirred reaction mixture was allowed to warm to room temperature for 3.5 h. The viscous reaction mixture was cooled in an ice-water bath and ice was added very slowly portionwise (Note: significant HCl was released upon addition of ice) followed by the slow addition of ice-water. The reaction mixture solidified upon quenching. The solid was filtered, washed with water, and allowed to stand overnight at RT. The solid was washed with water and triturated with hexanes (2×) to give a pink solid. The crude product was recrystallized from EtOAc to give a white solid. The solid was dried to give 16.0 g (60%) of compound 23 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 3.84 (s, 3H), 3.88 (s, 3H), 7.08 (d, J=8.8 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 8.08 (d, J=8.3 Hz, 2H).

Provenance & Evidence