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

HRID 437453ノート

反応式

HRID 437453 の反応式
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

参加物

3

反応物 2

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

生成物 1

HCID 27513302-(3-oxo-3-phenylpropyl)cyclohexanone収率 39.9%

実験手順

2-(3'-Phenyl-3'-oxopropyl)cyclohexanone was prepared accordinf to the method of W. Hahn and J. Epsztain (Roozniki 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. Found: C, 85.40; H.7.5; N, 6.9%, C15H15N requires: C, 86.00; H, 7.2; N, 6.7%

後処理

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

出典と根拠

ORDレコード
ord-9b3b78283cfe48ebb478d68c64f9fc98
出典データセット
uspto-grants-1977_06
特許番号
US04031102

反応ノート

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