Phthalic Anhydride → O-(p-Anisoyl)benzoic acid

Participants

Reaction Steps

Anhydrous aluminum chloride (140 g) was added at ambient temperature to a vigorously stirred mixture of 148 g of phthalic anhydride, 250 ml anisole, and 250 ml carbon disulfide. After 2.5 hours, the solution was hydrolyzed with ice water and the organic solvents were removed by steam distillation. A gray solid which precipitated when the residual solution cooled to room temperature was separated from the liquid by decantation and dissolved in ca. 1 L chloroform. Rotary evaporation of the chloroform left 107 g (42%) of white solid which was recrystallized from acetic acid/water: mp. 142°-144.5° C. (lit.* mp. 122°-123.5° C.). IR (KBr): 1686, 1660 (two different carbonyls), 1550-1600, 1420-1370, 1280, 1255, 1170, 1150, 1015, 850, 800, 755 cm-1.

Provenance & Evidence