Benzoyl chloride → 3-Benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one

HRID 846002Notes

Reaction equation

HRID 846002 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:8]1[C:9](=[O:24])[CH2:10][CH:11]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[CH2:12][C:13]=1[OH:14])[CH2:6][CH3:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(C(C)=O)C>[C:31]([O:24][C:9]1[CH2:10][CH:11]([C:15]2[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])[CH2:12][C:13](=[O:14])[C:8]=1[C:5](=[N:4][O:3][CH2:1][CH3:2])[CH2:6][CH3:7])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 1354748904-(1-(Ethoxyimino)propyl)-5-hydroxy-2',4',6'-trimethyl-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one

Product 1

HCID 736634413-Benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-oneYield 60.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (2.4 g), anhydrous methyl ethyl ketone (25 ml) and anhydrous potassium carbonate (1.65 g) was treated dropwise, with stirring, with benzoyl chloride (1.12 g). The mixture was heated under reflux with stirring for a period of 30 minutes and then filtered. The residue was washed with diethyl ether and the solvent from the combined filtrate and washings was evaporated under reduced pressure. The residue was taken up in ethyl acetate and the solution was washed twice with water, dried, and the solvent was evaporated under reduced pressure to give a dark brown oil. The oil was purified by chromatography on preparative thin layer chromatography plates (silica gel; eluent hexane/diethyl ether 75:25) to give 3-benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one (1.9 g).

Workup

  1. additionwas treated dropwise
  2. temperatureThe mixture was heated
  3. temperatureunder reflux
  4. filtrationfiltered
  5. washThe residue was washed with diethyl ether
  6. customthe solvent from the combined filtrate and washings was evaporated under reduced pressure
  7. washthe solution was washed twice with water
  8. customdried
  9. customthe solvent was evaporated under reduced pressure
  10. customto give a dark brown oil
  11. customThe oil was purified by chromatography on preparative thin layer chromatography plates (silica gel; eluent hexane/diethyl ether 75:25)

Sources & evidence

ORD record
ord-1e418eaf60c144a688823e4612aea162
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

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