Acetic Anhydride → cis-1,3-Cyclohexanedicarboxylic anhydride

Participants

Reaction Conditions

Reaction Steps

1,3-Cyclohexanedicarboxylic acid (mixture of cis and trans; 20 g; 0.116 mol) was slurried in acetic anhydride (80 mL; 0.85 mol; 7.3 equiv). The resulting mixture was heated to reflux (at which point it was homogeneous) for 5 h. A distillation head was added and the volatiles were removed by increasing the pot temperature to 200° C. Once no more distillate was collected the residue was cooled to ambient temperature to afford a solid mass. The crude product was recrystallized from hot toluene (40 mL) by the addition of heptane (40 mL) and cooling to 4° C. The precipitated product was filtered, washed with heptane, and dried in vacuo to afford 16.74 g (93%) of 1.

Provenance & Evidence