Water → Methyl 2-[(chlorosulfonyl)methyl]benzoate

HRID 325119Notes

Reaction equation

HRID 325119 reaction equation
O.O.O.O.O.O.[S:7]([O-:11])([O-])(=[O:9])=S.[Na+].[Na+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Cl.[Cl:26]Cl>C(O)(=O)C>[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][S:7]([Cl:26])(=[O:11])=[O:9])([O:15][CH3:14])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24526ChlorineHCID 61475Sodium Thiosulfate PentahydrateHCID 118590Methyl 2-chloromethylbenzoate

Product 1

HCID 10857839Methyl 2-[(chlorosulfonyl)methyl]benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of water (50 ml) and 29.5 g of sodium thiosulfate pentahydrate was added to o-(chloromethyl)benzoic acid methyl ester 20 g, and stirred for 5 hours at 50˜55° C. 300 ml of acetic acid was added and then excess of chlorine gas for 3 hours was infused, while maintaining the internal temperature of reactor at 5˜10° C. The reaction mixture was further stirred for 1 hour at the same temperature. Excess of chlorine gas was removed via infusion of nitrogen gas and with the addition of ice water (300 ml), stirred for 30 minutes. A solid, so formed, was filtered with a cold water and dried to afford 22.4 g of desired compound (yield 83%) as a white solid.

Workup

  1. temperaturewhile maintaining the internal temperature of reactor at 5˜10° C
  2. stirringThe reaction mixture was further stirred for 1 hour at the same temperature
  3. customExcess of chlorine gas was removed via infusion of nitrogen gas and with the addition of ice water (300 ml)
  4. stirringstirred for 30 minutes
  5. customA solid, so formed
  6. filtrationwas filtered with a cold water
  7. customdried

Sources & evidence

ORD record
ord-03f995e3028f4f0dac76202d2a66d46c
Source dataset
uspto-grants-2001_04
Patent number
US06222060B1

Reaction notes

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