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Hydrochloric Acid → Ethyl 3-oxo-2-(3-oxocyclohexyl)-3-phenylpropanoate

HRID 47078
Notes
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Reaction equation

HRID 47078 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:7].[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1.Cl>C1(C)C=CC=CC=1>[C:9]([CH:8]([CH:19]1[CH2:20][CH2:21][CH2:22][C:17](=[O:23])[CH2:18]1)[C:6]([O:5][CH2:4][CH3:3])=[O:7])(=[O:10])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 135942-Cyclohexen-1-oneHCID 24758Sodium hydride

Product 1

HCID 11323689Ethyl 3-oxo-2-(3-oxocyclohexyl)-3-phenylpropanoateYield 67%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a suspension of 60 mg (0.0025 mole) of sodium hydride in 7 ml of toluene was added 4.32 ml (0.025 mole) of ethyl benzoyl acetate. After several minutes a solution was obtained to which was added 2.41 ml (0.025 mole) of cyclohexenone. The reaction was stirred 36 hrs. at room temperature and then added to 25 ml 1 N hydrochloric acid--25 ml saturated sodium chloride--150 ml ether. The ether extract was dried over magnesium sulfate and evaporated to an oil. This crude oil was purified via column chromatography on 300 g of silica gel eluted with 50% ether--pentane to yield 4.8 g (67%) of the title compound as an oil.

Workup

  1. customAfter several minutes a solution was obtained to which
  2. extractionThe ether extract
  3. dry with materialwas dried over magnesium sulfate
  4. customevaporated to an oil
  5. customThis crude oil was purified via column chromatography on 300 g of silica gel
  6. washeluted with 50% ether

Sources & evidence

ORD record
ord-4cfc6ef6a1124b54b5af0627233a7b15
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04176196

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes