1,3-Cyclohexanedione → Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-

HRID 324719

Reaction equation

HRID 324719 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](C1C(=O)CCCC1=O)=[O:5].[Cl:22]C1C=C(S(C)(=O)=O)C=CC=1C(O)=O.S(Cl)(Cl)=O.C1(=O)CCCC(=O)C1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.N1C=NC=N1>[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]([Cl:22])=[O:5]

Participants

8

Reactant 5

HCID 104341,3-CyclohexanedioneHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 91760SulcotrioneHCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

Product 1

HCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-Yield 83.6%

Reagents, catalysts & solvents 2

HCID 92571H-1,2,4-TriazoleCatalystHCID 6342AcetonitrileSolvent2×

Procedure

2-(2-Chloro-4-methanesulphonylbenzoyl)-1,3-cyclohexanedione from the acid chloride. 2-Chloro-4-methanesulphonylbenzoyl chloride (5 g) was prepared by the reaction of 2-chloro-4-methanesulphonylbenzoic acid with thionyl chloride. The acid chloride was dissolved in acetonitrile (40 ml). A mixture of 1,3-cyclohexanedione (2.24 g), potassium carbonate (6.9 g) and acetonitrile (40 ml) was stirred at room temperature for 4 hours. To this solution was added the acid chloride solution over 10 min and allowed to stir 1 hour. 1,2,4-Triazole (0.07 g) was then added and the mixture allowed to stir 16 hours at room temperature. The solvent was removed and the residue was dissolved in water and acidified. The product was extracted into dichloromethane and the solvent was dried then evaporated to give the desired product in 83.6% yield.

Workup

  1. stirringto stir 1 hour
  2. stirringto stir 16 hours at room temperature
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in water
  5. extractionThe product was extracted into dichloromethane
  6. customthe solvent was dried
  7. customthen evaporated

Sources & evidence

ORD record
ord-4c98c7e96af84206acf08bce6722fb9e
Source dataset
uspto-grants-2001_04
Patent number
US06218579B1

Linked notes

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