Veratrole → HCID 14028056, compound

Participants

Reaction Conditions

Reaction Steps

To polyphosphoric acid (76 g) was added 1,2-dimethoxybenzene (7.9 g, 0.057 mol) followed by cyclopentanecarboxylic acid (9.8 g, 0.086 mol). The mixture was stirred at 60° C. during 24 hours then cooled down to −5° C. and quenched by the addition of 200 ml ice/water followed by 100 ml of ether. After stirring at room temperature for 3 hours, the two layers were separated and the aqueous phase extracted with three 100 ml portions of ether. The two ethereal phases were combined, washed with 50 ml of NaOH and 50 ml of brine and dried over MgSO4. Filtration and concentration gave 15.5 g of dark brown oil. This oil was purified by vacuum distillation (180-190° C., 0.03 mbar) through a short path to give 11.8 g (88%) of a white solid.

Provenance & Evidence