Dimethyl Sulfate → Methyl 3-methoxy-4-phenylthiobenzoate

HRID 37146Notes

Reaction equation

HRID 37146 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 49.11 g of methyl 3-hydroxy-4-phenylthiobenzoate, 27.33 g of potassium carbonate and 627 ml of acetone, 17.85 ml of dimethyl sulfate was added, and the mixture was refluxed for 6 hours while stirring. The reaction mixture was cooled, and the precipitate was filtered and washed with acetone. The filtrate and washing liquid were combined, and concentrated in vacuo, and methyl 3-methoxy-4-phenylthiobenzoate was obtained.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitate was filtered
  5. washwashed with acetone
  6. washThe filtrate and washing liquid
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9698a3f3190349ef858ae41864f5cab5
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Reaction notes

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