Ethyl benzoate → 1,3-Dicyclohexyl-1,3-propanedione

Participants

Reaction Steps

Other β-diketones can be prepared from esters and ketones containing R3 and R5 as previously defined. Thus, 1-cyclopropyl-3-phenyl-1,3-propanedione has been reported by G. W. Cannon et al., Journal of Organic Chemistry 17, 685 (1952) to be prepared as a solid, melting point 36°C to 37°C, from ethyl benzoate and cyclopropyl methylketone in the presence of sodium amide. Alternatively, it has been found that the same compound, melting point 38°C to 40°C, could be prepared from ethyl cyclopropanecarboxylate, acetophenone and sodium hydride. J. T. Adams and C. R. Hauser in Journal of the American Chemical Society 66, 1220 (1944) have prepared a series of 1-alkyl-3-phenyl-1,3-propanediones from carboxylic acid ethyl esters and acetophenone in the presence of sodium amide. Illustrative examples are tabulated employing the following equation: ##EQU2## where R3 and R5 are set forth in the Table I below.

Provenance & Evidence