Phthalic Anhydride → 2-(2,4-Dimethylbenzoyl)benzoic acid

Participants

Reaction Steps

An ice/salt cold mixture of m-xylene (114 g, 1073 mmol) was treated with aluminium chloride (59.4 g, 446 mmol) (in three portions), followed by 2-benzofuran-1,3-dione (30 g, 203 mmol) (in three portions). The mixture was warmed to room temperature and stirred for 3 hours after which time the mixture turned to a thick white suspension. The mixture was heated to 55° C. for 2 hours, and cooled to room temperature. The thick mixture was slowly poured into ice cold 20% HCl and collected on filter paper. The filtered material was allowed to dry to give the desired product as a white solid (50 g, 97%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.98-8.07 (m, 1 H) 7.60-7.69 (m, 1 H) 7.51-7.59 (m, 1 H) 7.38-7.45 (m, 1 H) 7.01-7.13 (m, 2 H) 6.86-6.94 (m, 1 H) 2.61 (s, 3 H) 2.33 (s, 3 H); LC/MS (m/z) ES+=255 (M+1).

Provenance & Evidence