Methyl 4-chloro-2-(chlorosulphonyl)benzoate → 52948-12-6

HRID 1241238Notes

Reaction equation

HRID 1241238 reaction equation
Cl[S:2]([C:5]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=O)=O>Cl.[Zn]>[SH:2][C:5]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 3020661Methyl 4-chloro-2-(chlorosulphonyl)benzoate

Product 1

HCID 1565712452948-12-6

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were added a little at a time to a suspension of 205 g (0.75 mol) of methyl 2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloric acid and 375 g of ice. The mixture was stirred for another 3 hours and slowly heated to 70° C. After 2 hours at this temperature, the mixture was cooled. The reaction mixture was allowed to stand at room temperature for 12 hours and then extracted with ethyl acetate, the combined organic phases were dried and the solvent was removed. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

Workup

  1. waitAfter 2 hours at this temperature
  2. temperaturethe mixture was cooled
  3. waitto stand at room temperature for 12 hours
  4. extractionextracted with ethyl acetate
  5. customthe combined organic phases were dried
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-cfd27acc07684b6b8c7ec8e9f58ee4c1
Source dataset
uspto-grants-2006_10
Patent number
US07115545B1

Reaction notes

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