Methanol → Methyl 4-chloro-3-mercapto-2-methylbenzoate

HRID 548590Notes

Reaction equation

HRID 548590 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[SH:12].[CH3:13]O>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[C:4]([CH3:11])[C:3]=1[SH:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 667391434-Chloro-3-mercapto-2-methylbenzoic acid

Product 1

HCID 67158973Methyl 4-chloro-3-mercapto-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Under an atmosphere of nitrogen, 3.60 g (17.8 mmol) of 4-chloro-3-mercapto-2-methylbenzoic acid in 50 ml of absolute methanol and 1 ml of concentrated sulfuric acid were heated under reflux for 17 h. The mixture was freed from solvent, and the residue was taken up in water. After two extractions with ethyl acetate, the combined organic phases were dried, filtered under an atmosphere of nitrogen and freed from the solvent. What was isolated were 3.2 g of pure product.

Workup

  1. temperatureunder reflux for 17 h
  2. extractionAfter two extractions with ethyl acetate
  3. customthe combined organic phases were dried
  4. filtrationfiltered under an atmosphere of nitrogen
  5. customWhat was isolated

Sources & evidence

ORD record
ord-6d856e14df4a4ee1968b35f8c1ac6b7c
Source dataset
uspto-grants-2011_05
Patent number
US07943551B2

Reaction notes

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