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

HRID 1370168Notes

Reaction equation

HRID 1370168 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. Stirring was continued for 3 hours, and the mixture was then 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 [lacuna] and the solvent was removed. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

Workup

  1. waitwas continued for 3 hours
  2. waitAfter 2 hours at this temperature
  3. temperaturethe mixture was cooled
  4. waitto stand at room temperature for 12 hours
  5. extractionextracted with ethyl acetate
  6. customthe combined organic phases [lacuna] and the solvent was removed

Sources & evidence

ORD record
ord-71f1d83a0c8f4e129ab5dff463ef154e
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

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