Hypochlorite → Methyl 2,4-dichloro-3-(3-t-butyl-4,5-dihydroisoxazol-5-yl)benzoate

HRID 859098Notes

Reaction equation

HRID 859098 reaction equation
Cl[O-].[Na+].[Cl:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([Cl:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:18][C:19]([CH3:24])([CH3:23])[CH:20]=[N:21][OH:22].Cl[O-]>ClCCl.O>[Cl:4][C:5]1[C:14]([CH:15]2[O:22][N:21]=[C:20]([C:19]([CH3:24])([CH3:23])[CH3:18])[CH2:16]2)=[C:13]([Cl:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 61739HypochloriteHCID 136457PivalaldoximeHCID 18769998Methyl 2,4-dichloro-3-ethenylbenzoateHCID 23665760Sodium Hypochlorite

Product 1

HCID 18770001Methyl 2,4-dichloro-3-(3-t-butyl-4,5-dihydroisoxazol-5-yl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

At room temperature, 17 ml of a 12% strength aqueous sodium hypochlorite solution were added dropwise with vigorous stirring to a solution of 2.6 g (10 mmol) of methyl 2,4-dichloro-3-ethenylbenzoate and 1 g (10 mmol) of 2,2-dimethylpropionaldoxime in 100 ml of dichloromethane. Twice, in each case after 2 hours of stirring, a further 0.5 g (5 mmol) of the oxime and 9 ml of the hypochlorite solution were added. The reaction mixture was stirred at room temperature for a further 12 hours and then stirred into 350 ml of water. After extraction with dichloromethane, drying and removal of the solvent, the residue was chromatographed.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for a further 12 hours
  2. extractionAfter extraction with dichloromethane
  3. customdrying
  4. customremoval of the solvent
  5. customthe residue was chromatographed

Sources & evidence

ORD record
ord-5fa49c6a40804c33a8442e2eb1ec76b4
Source dataset
uspto-grants-2006_12
Patent number
US07151075B2

Reaction notes

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