Ethylene → Methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

HRID 1276112Notes

Reaction equation

HRID 1276112 reaction equation
C=C.[Cl:3][C:4]1[C:13]([CH:14]=[N:15][OH:16])=[C:12]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[C:21]([O-])(=O)[CH3:22].[Na+].Cl[O-].[Na+]>ClCCl>[Cl:3][C:4]1[C:13]([C:14]2[CH2:22][CH2:21][O:16][N:15]=2)=[C:12]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 6325Ethylene3×HCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 22114925Methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoateYield 2,525.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 15-20° C., ethylene is introduced into a solution of 158.0 g (0.54 mol) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 1 l of dichloromethane for 30 minutes. After the addition of 1.6 g of sodium acetate, 454 ml of sodium hypochlorite solution were added dropwise at 10° C., while simultaneously introducing ethylene. Subsequently, ethylene was introduced at 10° C. for a further 15 minutes. The mixture was stirred for 12 hours, the phases were separated and the organic phase was washed with water, dried and concentrated. 156.5 g (90% of theory) of methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate were obtained.

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-47297133973d414e88c986553dc044a8
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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