Ethyl chloroacetate → Ethyl sulfoacetate

HRID 553462

Reaction equation

HRID 553462 reaction equation
[O-:1][S:2]([O-:4])=[O:3].[Na+].[Na+].Cl[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>O.CCO>[CH2:12]([O:11][C:9]([CH2:8][S:2]([OH:4])(=[O:1])=[O:3])=[O:10])[CH3:13]

Participants

5

Reactant 2

HCID 7751Ethyl chloroacetateHCID 24437Sodium Sulfite

Product 1

HCID 12216623Ethyl sulfoacetateYield 100.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Na2SO3 (10 g, 79 mmol.) in 50 mL of H2O was added a solution of ethyl 2-chloroacetate (12.7 mL, 119 mmol.) in 55 mL of EtOH. The mixture was heated at reflux for 6 h, after which time all the volatiles were removed by evaporation under reduced pressure. The concentrated materials were dried to afford crude (ethoxycarbonyl)methanesulfonic acid (13.3 g, 100%) used directly without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. customafter which time all the volatiles were removed by evaporation under reduced pressure
  4. customThe concentrated materials were dried

Sources & evidence

ORD record
ord-c88b6db0b6db47158d18750b41bcb397
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Linked notes

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