Cyclohexanone → 2-(3-oxo-3-phenylpropyl)cyclohexanone

HRID 596468Notes

Reaction equation

HRID 596468 reaction equation
CN(C)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[C:7]1([C:5](=[O:6])[CH2:4][CH2:3][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:14]2=[O:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 7967CyclohexanoneHCID 770423-(Dimethylamino)-1-phenyl-1-propanone

Product 1

HCID 27513302-(3-oxo-3-phenylpropyl)cyclohexanoneYield 39.9%

Procedure

2-(3'-Phenyl-3'-oxopropyl)cyclohexanone was prepared according to the method of W. Hahn and J. Epsztain (Roczniki Chem. 1963, 37, 403-12): A mixture of β-dimethylaminopropiophenone (27 gm.) and cyclohexanone (37.5 g.) were heated at reflux for 5 hours under nitrogen and the solvent removed in vacuo. The residual oil was distilled giving 2-(3'-phenyl-3'-oxopropyl)cyclohexanone (14 g.) which was cyclised to the title compound according to the method of Hahn and Epsztain by dissolving the diketone (12 g.) in ethanol (65 ml.), treating with hydroxylamine hydrochloride (9 g.) and heating under reflux for 1 hour. The cooled reaction mixture was poured onto water (300 ml.), extracted with ether (2 × 50 ml.) and the extracts discarded. The aqueous solution was made basic with K2CO3 and extracted with ether (3 × 50 ml.). The combined ether extracts were dried and the solvent removed in vacuo. The residual oil was distilled to give the title compound as a colourless oil (7 g.) b.p. 134°-8° C/15 mm.

Workup

  1. custom2-(3'-Phenyl-3'-oxopropyl)cyclohexanone was prepared
  2. temperaturewere heated
  3. temperatureat reflux for 5 hours under nitrogen
  4. customthe solvent removed in vacuo
  5. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-305a4f9bfaf64c96ad5aa98cb405bad2
Source dataset
uspto-grants-1977_03
Patent number
US04011225

Reaction notes

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