Bulletin of the Chemical Society of Japan p. 2361 - 2365 (1985)
Update date:2022-07-30
Topics:
Uneyama, Kenji
Masatsugu, Yosinori
Torii, Sigeru
Electrooxidative carbon-carbon bond cleavage is useful for the preparation of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid (1b) from 3-methyl-2-phenyl-8-(1-propenyl)-4H-benzopyran-4-one (2).Olefin 2 was transformed into 3-methyl-8-(1,2-epoxypropyl)-3-methyl-2-phenyl-4H-1-benzopyran-4-one (3) by the electrochemical bromohydrination in an MeCN-H2O-H2SO4-NaBr-(Pt) system followed by treatment of aqueous sodium hydroxide (94percent).The epoxide 3 was electrooxidized in an MeOH-H2SO4-(C) system, affording 8-formyl-3-methyl-2-phenyl-4H-1-benzopyran-4-one (4) in 83percent yield.Hydrogen peroxide oxidation of 4 in refluxing 2-butanone gave 1b in 86percent yield.
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