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

HRID 846000Notes

Reaction equation

HRID 846000 reaction equation
[OH-].[Na+].[CH2:3]([O:5][N:6]=[C:7]([C:10]1[C:11](=[O:26])[CH2:12][CH:13]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH2:14][C:15]=1[OH:16])[CH2:8][CH3:9])[CH3:4].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O>[C:27]([O:26][C:11]1[CH2:12][CH:13]([C:17]2[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=2[CH3:23])[CH2:14][C:15](=[O:16])[C:10]=1[C:7](=[N:6][O:5][CH2:3][CH3:4])[CH2:8][CH3:9])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 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 68.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Aqueous 1% sodium hydroxide solution (6 ml) was added to a solution of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (0.42 g; 1.28 mmole) in acetone (50 ml). The mixture was stirred at room temperature for a period of 5 minutes and then benzoyl chloride (0.2 g) was added dropwise. The mixture was stirred for a further period of 15 minutes and then the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The product was purified by chromatography over silica gel (eluant dichloromethane) to give 3-benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one (0.38 g; 68.6%) as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred for a further period of 15 minutes
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customa rotary evaporator
  4. customThe product was purified by chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-8961b40b7b6946f5988b6b103a8a2bde
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

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