Chloroacetic Acid → p-Tolyl methyl sulfone

HRID 21843

Reaction equation

HRID 21843 reaction equation
S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[Na].Cl[CH2:25]C(O)=O>O>[CH3:25][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 73974-Toluenesulfonyl chlorideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 5360545Sodium

Product 1

HCID 18521p-Tolyl methyl sulfone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
15 °C

Procedure

176.4 g of sodium sulfite and 226 g of sodium bicarbonate were dissolved in 1800 ml of water and cooled down to 15° C. 244 g of p-toluenesulfonyl chloride were added at that temperature with thorough stirring. The mixture was additionally stirred for 3 hours at 15° C. and overnight at room temperature. It was then heated to 40° C. and a solution of 175 g of the sodium salt of chloroacetic acid in 400 ml of water was added. The reaction mixture was stirred under reflux for 24 hours. After cooling down to 5°-10° C. the precipitated product was filtered off with suction and dried at 50° C. under reduced pressure, leaving 192.5 g of 4-methylsulfonyltoluene (melting point 83°-86° C).

Workup

  1. temperatureIt was then heated to 40° C.
  2. stirringThe reaction mixture was stirred
  3. temperatureunder reflux for 24 hours
  4. temperatureAfter cooling down to 5°-10° C. the precipitated product
  5. filtrationwas filtered off with suction
  6. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-93ce9765970742b183f35d6e6820cfb0
Source dataset
uspto-grants-1995_06
Patent number
US05424481

Linked notes

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