1-cyclopropyl-3-phenylpropane-1,3-dione

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetophenone (10.1 g; 0.084 mol) and MCPC (25.2 g; 0.25 mol; 3 equiv) were dissolved in DMSO (46.1 g). Sodium methoxide (9.1 g; 0.168 mol; 2.0 equiv) was added slowly while maintaining the temperature below 30° C. The reaction mixture was then heated to 40° C. for 5 h. Heptane (100 mL) was added followed by sufficient 20% aqueous HCl such that the pH was less than 5. The mixture was stirred for 15 min and then allowed to settle. The lower aqueous layer was decanted and discarded. The upper organic layer was washed with 40 mL of water, and the solvent was stripped to afford 14 g of crude 8, which was 97.2% pure by GC (area %) to afford an 86% yield of 8. while maintaining the temperature below 30° C The lower aqueous layer was decanted The upper organic layer was washed with 40 mL of water to afford 14 g of crude 8, which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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.