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

HRID 2083405노트

반응식

HRID 2083405 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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. Found: C, 85.40; H, 7.5; N, 6.9%, C15H15N requires: C, 86.00; H, 7.2; N, 6.7%.

후처리

  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

출처 및 근거

ORD 기록
ord-ae6262d99efe4e7ca733ca4388c73109
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04085215

반응 노트

불러오는 중…