Acetic Anhydride → Homophthalic anhydride

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask containing a stirring bar was charged with homophthalic acid (2.0 g, 11.101 mmol). Acetic anhydride (25.0 mL) was added, the flask was fitted with a condenser and the reaction mixture was heated at 80° C. for 2 h. The excess acetic anhydride was removed in vacuo and the solid obtained was triturated with Et2O (10.0 mL), filtered and dried to obtain homophthalic anhydride as an off white solid (1.53 g, 85%). Spectral data for this compound were consistent with those in the literature. M.p. 140-144° C. (lit. m.p. 140-145° C.); 1H NMR (400 MHz, DMSO-d6): δ=8.05 (d, J=8.2 Hz, 1H), 7.75 (app. t, 1H), 7.52 (app. t, 1H), 7.44 (d, J=7.8 Hz, 1H), 4.27 (s, 2H).

Provenance & Evidence