Dimethyl Sulfate → Methyl 3-methoxy-4-phenylthiobenzoate

HRID 621632Notes

Reaction equation

HRID 621632 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH3:8])=[S:6].[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:18][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][CH3:8])=[S:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54152449Methyl 3-hydroxy-4-phenylthiobenzoate

Product 1

HCID 53705693Methyl 3-methoxy-4-phenylthiobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of methyl 3-hyroxy-4-phenylthiobenzoate (49.11 g), potassium carbonate (27.33 g) and acetone (627 ml) is added dimethyl sulfate (17.85 ml), and the mixture is refluxed with stirring for 6 hours. The reaction mixture is cooled, and the precipitate is separated by filtration and washed with acetone. The filtrate and washings are combined and concentrated under reduced pressure to give methyl 3-methoxy-4-phenylthiobenzoate.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureThe reaction mixture is cooled
  3. customthe precipitate is separated by filtration
  4. washwashed with acetone
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8440b4cb552d42218a6e6e287f51bd36
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

Loading…