Cyclohexanone → 2-(3-oxo-3-phenylpropyl)cyclohexanone
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]=1Participants
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.) amd 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. Found: C, 85.40; H, 7.5; N, 6.9%, C15H15N requires: C, 86.00; H, 7.2; N, 6.7%.
Workup
- custom2-(3'-Phenyl-3'-oxopropyl)cyclohexanone was prepared
- temperaturewere heated
- temperatureat reflux for 5 hours under nitrogen
- customthe solvent removed in vacuo
- distillationThe residual oil was distilled
Sources & evidence
- ORD record
- ord-8c581870a2a44f9383c10055dcc9f773
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04044138
Reaction notes
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