Benzaldehyde → 1,2-Diphenylpentane-1,4-dione

Participants

Reaction Steps

A solution of 21.2 g (0.2 mol) of benzaldehyde and 100 ml of absolute dimethylformamide is added dropwise in the course of 1/2 hour to a mixture of 4.9 g (0.1 mol) of NaCN and 100 ml of absolute dimethylformamide in a manner analgous to Example 3. Stirring is then continued for 11/2 hours at 35° C. A solution of 21.9 g (0.15 mol) of benzalacetone and 100 ml of dimethylformamide is then slowly added dropwise in the course of 31/2 hours at 35° C. Stirring is then continued for 31/2 hours at the same temperature. The reaction mixture is treated with twice its quantity of water and the product is worked up in a manner analogous to Example 5. 43.5 g of crude product are obtained from which 25.2 g of 1,4-dioxo-1,2-diphenyl-pentane (67% of theoretical) are obtained by distillation. B.p.: 166° C/0.4 mm Hg; m.p.: 60°-61° C C17H16O2 (253.3) Calculated: C, 80.92; H, 6.39. Found: C, 80.62; H, 6.50.

Provenance & Evidence