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14.4.3.1.1.2.1.1.2 Variation 2: Condensation of 2-Hydroxyphenyl Ketones with Acyl Chlorides

DOI: 10.1055/sos-SD-014-00294

Williams, A. C.; Camp, N.Science of Synthesis, (200314450.

Examples of the condensation of 2-hydroxyphenyl ketones with acyl chlorides to give 4H-1-benzopyran-4-ones are given in Schemes 101103. Condensation of a 2-hydroxyphenyl ketone with a benzoyl chloride using potassium tert-butoxide gives an intermediate 1-(2-hydroxyphenyl)-3-arylpropane-1,3-dione 302; on refluxing with sulfuric acid in acetic acid, 302 gives the 2-aryl-4H-1-benzopyran-4-one 303 in poor to moderate yield. An analogous reaction using lithium hexamethylsilazanide as the base gives intermediate 304 and final cyclization product 305 in excellent yield. Condensation of 1-(2-hydroxy-4-methoxyphenyl)-4-phenylbutan-1-one with 3,4-dimethoxybenzoyl chloride gives 1-[2-(3,4-dimethoxybenzoyloxy)-4-methoxyphenyl]-4-phenylbutan-1-one (306), which cyclizes to give 2-(3,4-dimethoxyphenyl)-7-methoxy-3-(2-phenylethyl)-4H-1-benzopyran-4-one (307); similarly a 1-(2,4-dihydroxyphenyl)-2-benzimidazol-2-ylethanone gives 308 as an intermediate, which cyclizes to 309 on treatment with hydrochloric acid in ethanol. Other examples of the condensation of 2-hydroxyphenyl ketones with benzoyl or acyl chlorides include the formation of 310320.

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References