Dibenzylidene acetone → 1,5-Diphenylpentan-3-ol

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Reaction Steps

A mixture of 1.00 g (4.27 mmol) of dibenzylidene acetone and 0.15 g of 10% palladium on carbon in 150 ml of methyl cellusolve was shaken under 4 atm. of hydrogen for 2 h. The solution was filtered and concentrated in vacuo. Flash chromatography using 10-20% ethyl acetate in hexane gave 0.60 g (59%) of 1,5-diphenyl-3-pentanone (Rf 0.43, 20% ethyl acetate in hexane) as a colorless Oil and 0.29 g (28%) of 1,5-diphenyl-3-pentanol (Rf 0.36) as a white solid, m.p. 43°-5° C. 1,5-Diphenyl-3-pentanone: 1H NMR (CDCl3) δ 2.71 (t, J=7 Hz, 4H), 2.89 (t, J=7 Hz, 4H), 7.1-7.3 (m, 10H). Mass spectrum (M+NH4)+ 256.

Provenance & Evidence