Sodium Hydroxide → 1-Phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione

HRID 1725184

반응식

HRID 1725184 반응식
C(OC(=O)[CH:5]([C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]1)=[O:16])[CH2:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[C:8]1([C:7](=[O:14])[CH2:6][CH2:5][C:15]([CH:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21][CH2:22]2)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 690616894-Oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester

생성물 1

HCID 574237211-Phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione수율 23.6%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 7.63 g (21.3 mmol) 4-oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester in 66 mL toluene was added 36 mL 3M aqueous sodium hydroxide and 0.32 g (0.96 mmol) tetra-n-butylammonium hydrogen sulfate. The reaction was heated to reflux over 16 hr, allowed to cool and poured into brine. The solution was extracted two times with ether and concentrated to give an oil. The crude product was chromatographed on silica to give 1.44 g 1-phenyl-4-(4-propyl-cyclohexyl)-butane-1,4-dione as a red solid.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux over 16 hr
  3. temperatureto cool
  4. extractionThe solution was extracted two times with ether
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude product was chromatographed on silica

출처 및 근거

ORD 기록
ord-2775bc07a7644e7a8c9e824f089b1ddc
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488832B2

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