Methacrylic Acid → 6-Isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 39.3 g (0.46 mol) of methacrylic acid and 115 g (0.38 mol) of 1-(pentafluorophenoxy)-2-isopropylbenzene was added dropwise to Eaton's reagent (prepared from 99 g of P4O10 and 500 ml of MeSO3H) for 1 h at 70° C. The resulting mixture was stirred at 70° C. for 1 h, then cooled to room temperature, and poured on 1000 cm3 of ice. The crude product was extracted with 3×200 ml of dichloromethane. The organic extract was washed with aqueous K2CO3, dried over Na2SO4, and then evaporated to dryness. The product was purified by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane=5:1, vol., then n-hexane-dichloromethane-ether=50:25:1, vol.) to give 30.1 g (20%) of the title indanone. Additionally, 39.4 g of the starting 1-(pentafluorophenoxy)-2-isopropylbenzene was isolated also.

Provenance & Evidence