Water → 3-Allyl-2',6'-dichloro-biphenyl-2-ol

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Reaction Steps

A solution of 2′-(allyloxy)-2,6-dichloro-1,1′-biphenyl (5.7 g, 0.0204 mol) in anhydrous 1-methyl-2-pyrrolidinone (50 mL) was heated to 180° C. for 42 hours then at 190° C. for 5 days. The cooled reaction mixture was poured into water (300 mL), the mixture stirred vigorously for 15 minutes then the resulting oily suspension extracted with ethyl acetate (400 mL). The organic extract was washed with water (300 mL) and saturated brine (300 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford a brown oil. Purification by flash chromatography using a solvent gradient of 2 to 4% ethyl acetate in hexane gave 4.71 g (83%) of 3-allyl-2′,6′-dichloro-1,1′-biphenyl-2-ol as a colorless oil. MS (ES) m/z 278.9 ([M+H]+).

Provenance & Evidence