Methanol → HCID 53903945, compound

HRID 621639Notes

Reaction equation

HRID 621639 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[S:6].S(=O)(=O)(O)O.[CH3:22]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH3:22])=[S:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178427261HCID 178427261, compound

Product 1

HCID 53903945HCID 53903945, compound

Procedure

A mixture of 3-methyl-4-phenylthiobenzoic acid (85 g), conc. sulfuric acid (20 ml) and methanol (1.2 liter) is refluxed with stirring for 4 hours. After the reaction is completed, the reaction mixture is concentrated under reduced pressure. To the residue is added ethyl acetate (1.5 liter), and the mixture is washed with saturated aqueous sodium chloride solution (400 ml×3), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 3-methyl-4-phenylthiobenzoate (80.33 g).

Workup

  1. temperatureis refluxed
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionTo the residue is added ethyl acetate (1.5 liter)
  4. washthe mixture is washed with saturated aqueous sodium chloride solution (400 ml×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18a79a89b3b74a7b9a288e35b62e27d9
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

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