Butanal → Cinnamoylbenzene

HRID 258942

Reaction equation

HRID 258942 reaction equation
[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH:6](=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)C=O.C(N(CC)CC)C>C(O)C>[CH:6](=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:16]1([C:14](=[O:15])[CH2:13][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 261ButanalHCID 6228DimethylformamideHCID 7189CinnamoylbenzeneHCID 8471Triethylamine

Product 2

HCID 7189CinnamoylbenzeneHCID 122882371,3-Diphenylheptane-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the description in Example 1, 18 g (0.25 mol) of n-butyraldehyde, 52 g (0.25 mol) of benzylideneacetophenone and 500 ml of dimethylformamide, 250 ml of ethanol and 13.5 g (0.05 mol) of Cat. 1 are -- after addition of 10.1 g (0.1 mol) of triethylamine -- brought to the reflux temperature for 36 hours. To work up the batch, the solvent mixture is distilled off in a waterpump vacuum, the oily residue, when cold, is taken up in 250 ml of chloroform and the solution is washed successively with water, with dilute sodium bisulphite solution and twice more with water. The organic phase is separated off, the chloroform is distilled off and the residue is distilled in an oil pump vacuum. The fraction of boiling point0.2 = 140° - 170° C which is thus obtained is subsequently fractionated through a 30 cm Vigreux column. After a first running of benzylideneacetophenone, 1,3-diphenylheptane-1,4-dione is isolated as the main fraction.

Workup

  1. distillationthe solvent mixture is distilled off in a waterpump vacuum
  2. washthe solution is washed successively with water, with dilute sodium bisulphite solution and twice more with water
  3. customThe organic phase is separated off
  4. distillationthe chloroform is distilled off
  5. distillationthe residue is distilled in an oil pump vacuum
  6. custompoint0.2 = 140° - 170° C which
  7. customis thus obtained

Sources & evidence

ORD record
ord-351b6be7b1054901aad685f1af361849
Source dataset
uspto-grants-1977_07
Patent number
US04035395

Linked notes

Loading…