Water → 3-Chloro-2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohex-2-en-1-one

HRID 1722191Notes

Reaction equation

HRID 1722191 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=O)=[O:5].C(Cl)(=O)C([Cl:25])=O.CN(C)C=O.O>C(Cl)Cl>[Cl:25][C:7]1[CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:6]=1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][C:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:17][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 91760Sulcotrione

Product 1

HCID 142799823-Chloro-2-[2-chloro-4-(methanesulfonyl)benzoyl]cyclohex-2-en-1-oneYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione (9.8 g, 30 millimole) was dissolved in 100 ml methylene chloride and stirred at room temperature. To this solution was added oxalyl chloride (5.7 g, 45 mmol) followed by dimethylformamide (0.5 ml) in portions small enough to control effervescence. The resulting solution was stirred for 4 hours and then poured into water and extracted with methylene chloride. The organic layer was washed again with water, saturated K2CO3 solution and then dried with MgSO4 and the solvent evaporated to yield 3-chloro-2-(2chloro-4-methanesulfonylbenzoyl)cyclohex-2-enone (7.3 g, 70%) as an oil which was used without further purification.

Workup

  1. stirringThe resulting solution was stirred for 4 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed again with water, saturated K2CO3 solution
  4. dry with materialdried with MgSO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-9a384d828db7487fa05b66f903116381
Source dataset
uspto-grants-1989_08
Patent number
US04854966

Reaction notes

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