Methanol → Methyl 3-methyl-6-(phenylthio)-benzoate

HRID 435605Notes

Reaction equation

HRID 435605 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:23]O>>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[C:5]([O:7][CH3:23])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 125390985-Methyl-2-(phenylsulfanyl)benzoic acid

Product 1

HCID 21481132Methyl 3-methyl-6-(phenylthio)-benzoate

Procedure

650 g of 3-methyl-6-(phenylthio)-benzoic acid in 7.5 litres of absolute methanol are slowly treated with 300 ml of concentrated sulphuric acid and the mixture is heated for 24 hours under reflux. The mixture is concentrated and the residue poured on to an ice-cold sodium bicarbonate solution. The mass is extracted with ether, washed with water, dried over sodium sulphate and concentrated. There is obtained methyl 3-methyl-6-(phenylthio)-benzoate as a red-brown oil which crystallises on standing.

Workup

  1. temperaturethe mixture is heated for 24 hours
  2. temperatureunder reflux
  3. concentrationThe mixture is concentrated
  4. additionthe residue poured on to an ice-cold sodium bicarbonate solution
  5. extractionThe mass is extracted with ether
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4688c237d58743a7af3a3ee3fdad7b57
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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