Sulfuryl chloride → Methyl 2-chloromethyl-6-methylbenzoate

HRID 1611744Notes

Reaction equation

HRID 1611744 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:16])(=O)=O.C([O-])(O)=O.[Na+]>ClC1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[Cl:16][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 519028Methyl 2,6-dimethylbenzoate

Product 1

HCID 22256029Methyl 2-chloromethyl-6-methylbenzoateYield 128.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 7964ChlorobenzeneSolvent

Procedure

11.9 g of methyl 2,6-dimethylbenzoate are initially charged in 50 ml of chlorobenzene admixed at room temperature with 8.2 g of sulfuryl chloride and 40 mg of AIBN. The mixture is stirred at 60–90° C. for 2 h. Afterwards, the mixture is admixed with 80 ml of saturated NaHCO3 solution. After the phase separation, the organic phase is washed with 100 ml of 10% Na2SO3 solution, the organic phase is dried over magnesium sulfate and the chlorobenzene is distilled off in vacuo. 15.5 g of colorless liquid are obtained. The product is distilled under high vacuum (0.1 mbar, 66–77° C.). Yield: 10.2 g (71% of theory; 95.2 area %).

Workup

  1. customAfter the phase separation
  2. washthe organic phase is washed with 100 ml of 10% Na2SO3 solution
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. distillationthe chlorobenzene is distilled off in vacuo

Sources & evidence

ORD record
ord-8823b39daf87422b946bb21ae9d0eb52
Source dataset
uspto-grants-2006_01
Patent number
US06989462B2

Reaction notes

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