4-Chlororesorcinol → HCID 67166662, compound

Participants

Reaction Steps

A solution of 4-chlorobenzene-1,3-diol (100 g, 692 mmol) and 3-chloropropanoic acid (75.1 g, 692 mmol) in trifluoromethanesulfonic acid (295 mL) was stirred at 75° C. for 30 minutes. The reaction was cooled to ambient temperature and slowly poured into a 2 L beaker filled with ice. To the slurry was added ethyl acetate (1200 mL) with stirring until all solids dissolved. The mixture was poured into a reparatory funnel, the aqueous layer was removed and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography eluting with a solvent system mixture of 15% ethyl acetate/hexanes to provide the desired product (162.6 g, 86%).

Provenance & Evidence