Estragole → 2-((4-Methoxyphenyl)methyl)oxirane

Participants

Reaction Steps

To a stirring solution of 4-allylanisole (3.1 g, 20.9 mmol) in 50 mL dichloromethane was added 3-chloroperoxybenzoic acid (80%, 6.7 g, 31.4 mmol) at room temperature. TLC (20:1 hexanes/ethyl acetate) showed no remaining allyl after 3 h. The precipitate was removed via filtration and washed with hexanes. The filtrate was purified on 40 g silica eluting with 0 to 10% ethyl acetate/hexanes to give the product. NMR CDCl3) d (1H, 2.55 ppm), m (2H, 2.7-2.8 ppm), dd (1H, 2.85 ppm), m (1H, 3.1 ppm), s (3H, 3.75 ppm), d (2H, 6.85 ppm), d (2H, 7.15 ppm).

Provenance & Evidence