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

HRID 597554Notes

Reaction equation

HRID 597554 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[C-]#N.[Na+].[CH:17](=[CH:24][C:25](=[O:27])[CH3:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[O:8]=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:24][C:25](=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6228Dimethylformamide3×HCID 8929Sodium CyanideHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 131847301,2-Diphenylpentane-1,4-dioneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. custom2 hours
  2. customat 35° C
  3. stirringStirring
  4. custom2 hours

Sources & evidence

ORD record
ord-7207dff3c081458a9c89c0a2283572cd
Source dataset
uspto-grants-1977_03
Patent number
US04014889

Reaction notes

Loading…