Quinone → 3-(3-Chlorophenyl)-7-methoxyisochromen-1-one

Participants

Reaction Steps

A solution of (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid (15.00 g, 51.95 mmol) in anhydrous THF (520 mL) was sparged with argon for 5 min. p-Benzoquinone (6.18 g, 57.20 mmol) was added followed by bis(acetonitrile)dichloropalladium(II) (674 mg, 2.60 mmol) and the resultant mixture stirred at ambient temperature for 17 h. 1 N NaOH (aq.) (375 mL) was added and the resultant brown solid washed with chloroform (4×200 mL) to provide 3-(3-chlorophenyl)-7-methoxyisochromen-1-one (10.96 g, 38.23 mmol, 74%) as pale yellow solid.

Provenance & Evidence