Chloroacetic Acid → 1,3-Dimethyl-5-(methylsulfonyl)benzene

HRID 2071028Notes

Reaction equation

HRID 2071028 reaction equation
[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+].[CH3:12][C:13]1[CH:14]=[C:15]([S:20](Cl)(=[O:22])=[O:21])[CH:16]=[C:17]([CH3:19])[CH:18]=1.Cl[CH2:25]C(O)=O.[OH-].[Na+].Cl>O>[CH3:12][C:13]1[CH:14]=[C:15]([S:20]([CH3:25])(=[O:22])=[O:21])[CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

8

Reactant 6

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27362353,5-Dimethylbenzenesulfonyl chloride

Product 1

HCID 27586201,3-Dimethyl-5-(methylsulfonyl)benzeneYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
135 °C

Procedure

To a stirring slurry of 3.2 g (25.4 mmol) of Na2SO3 and 6.2 g (73.8 mmol) of NaHCO3 in 20 mL of H2O at 75° C. was added 5.0 g (24.4 mmol) of 3,5-dimethylbenzene-1-sulfonyl chloride in several portions. After 2 h at 75° C., 3.5 g (37.0 mmol) of chloroacetic acid was added in portions followed by 1.5 g (37.5 mmol) of NaOH in 3 mL of H2O. The mixture was stirred at 135° C. for 13 h, and 3 N HCl was added to a pH=1. A colorless precipitate formed, and the mixture was filtered through a Buchner funnel to provide 3.8 g of 1,3-dimethyl-5-(methylsulfonyl)benzene in 84% yield.

Workup

  1. customA colorless precipitate formed
  2. filtrationthe mixture was filtered through a Buchner funnel

Sources & evidence

ORD record
ord-e1b67117e45e423db927907dc053de8a
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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