Benzoyl chloride → HCID 73771260, compound

HRID 1382170Notes

Reaction equation

HRID 1382170 reaction equation
[OH-].[Na+].[CH2:3]([O:5][N:6]=[C:7]([C:10]1[C:11](=[O:29])[CH2:12][CH:13]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[O:27][CH3:28])[CH2:14][C:15]=1[OH:16])[CH2:8][CH3:9])[CH3:4].[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[C:30]([O:29][C:11]1[CH2:12][CH:13]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[O:27][CH3:28])[CH2:14][C:15](=[O:16])[C:10]=1[C:7](=[N:6][O:5][CH2:3][CH3:4])[CH2:8][CH3:9])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 136082425HCID 136082425, compound

Product 1

HCID 73771260HCID 73771260, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Aqueous 1% sodium hydroxide solution (6.1 ml) was added to a solution of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethoxyphenyl)cyclohex-2-en-1-one (0.52 g; 1.40 mmole) in acetone (25 ml). The mixture was stirred at room temperature for a period of 5 minutes and then benzoyl chloride (0.21 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. The product was purified by chromatography over silica gel (eluant dichloromethane) to give 3-benzoyloxy-2-[1-(ethoxyimino)propyl]-5-(2,4,6-trimethoxyphenyl)cyclohex-2-en-1-one (0.50 g; 73.9%) as a pale yellow solid, mp 139° C.

Workup

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

Sources & evidence

ORD record
ord-a8062140e40c4fa9ad4ff6e62c77c635
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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