Benzoyl chloride → HCID 54347390, compound

HRID 1031324Notes

Reaction equation

HRID 1031324 reaction equation
[OH-].[Na+].[CH2:3]([O:6][N:7]=[C:8]([C:11]1[C:12](=[O:27])[CH2:13][C:14]([CH3:26])([CH3:25])[CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C:16]=1[OH:17])[CH2:9][CH3:10])[CH:4]=[CH2:5].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[CH2:3]([O:6][N:7]=[C:8]([C:11]1[C:12](=[O:27])[CH2:13][C:14]([CH3:26])([CH3:25])[CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C:16]=1[O:17][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:9][CH3:10])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 136099031HCID 136099031, compound

Product 1

HCID 54347390HCID 54347390, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Aqueous 1% sodium hydroxide (30 ml) was added to a stirred solution of 2-[1-(allyloxyimino)propyl-3-hydroxy-4-(3-chlorophenyl)-5,5-dimethyl-cyclohex-2-en-1-one (2.5 g) in acetone (200 ml). The mixture was stirred at ambient temperature for 5 minutes and then benzoyl chloride (1 g) in acetone (25 ml) was added dropwise. After 30 minutes the mixture was evaporated in vacuo and the residue purified on a silica gel column using methylene chloride as eluant to give the title compound (3.0 g) as a colourless oil.

Workup

  1. customAfter 30 minutes the mixture was evaporated in vacuo
  2. customthe residue purified on a silica gel column

Sources & evidence

ORD record
ord-a1763b280d6148a9b0c7240cfa432721
Source dataset
uspto-grants-1990_09
Patent number
US04954160

Reaction notes

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