Hydrochloric Acid → 2-Acetylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of phthalic anhydride (compound of formula (XII)) (2.3 kg, 1 eq) (commercially available), malonic acid (compound of formula (XIII)) (389 g) (commercially available) and triethylamine (3.2 L) were heated to 80° C. Further portions of malonic acid (5×389 g; 1.94 kg total) were charged at 15 minute intervals and the reaction mixture maintained at 80° C. for 10 hrs. 4M hydrochloric acid (12.2 L) was charged and the reaction stirred for a further 30 minutes before being cooled to 25° C. and the resulting slurry filtered. The damp cake was washed with water (2×4 L) before being dried in vacuo at 50° C. to give the title compound (1.73 kg, 68%); 1H NMR (400 MHz, CDCl3): δ 1.97 (3H, s, CH3), 4.13 (1H, br s, OH) 7.52-7.63 (2H, m, CH Ar), 7.69-7.73 (1H, t, CH Ar), 7.84-7.86 (1H, d, CH Ar); 13C NMR (100 MHz, CDCl3) δ 26.0, 106.6, 122.1, 125.4, 126.0, 130.5, 134.8, 149.8 and 169.3.

Provenance & Evidence