Sulfuric Acid → 2-Phenyl-5-methoxy-6,7-dichloro-1-indanone

Participants

Reaction Steps

2',3' -Dichloro-4'-methoxy-2-phenylacrylophenone (160 g.) dissolved in dichloromethane (4 liters) is added dropwise to a mixture of 12N sulfuric acid (2 liters) and dichloromethane (2 liters) at <5°C. over a 3-hour period. The reaction mixture is stirred for an additional 30 minutes then poured slowly onto crushed ice. The dichloromethane layer is separated, washed with saturated sodium chloride solution, then dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure leaving a light tan solid residue. On drying in a steam oven at 70°C., 120.5 g. of product (75%) is obtained, mp 187°-192°C. A sample recrystallized from benzene-cyclohexane (2:1) melts at 193°-195°C.

Provenance & Evidence