Water → Di-n-propyl cis-1,3-cyclohexanedicarboxylate

Participants

Reaction Steps

Anhydride 1 (3.85 g; 25 mmol) was dissolved in toluene (25 mL) and n-propanol (9.3 mL; 125 mmol; 5 equiv). p-Toluenesulfonic acid (238 mg; 1.25 mmol; 0.05 equiv) was added and the reaction mixture was heated to reflux under conditions where water could be continuously distilled using a Dean-Stark trap. After 2 h at reflux, GC analysis indicated no residual 1. The reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL). The organic solution was dried over MgSO4 and concentrated to afford 6.24 g (97%) of cis-2c which was a single peak by GC analysis.

Provenance & Evidence