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

HRID 1725184Notes

Reaction equation

HRID 1725184 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2775bc07a7644e7a8c9e824f089b1ddc
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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