Methanol → Methyl 2-(4-(methylsulfonyl)phenyl)acetate

HRID 453087Notes

Reaction equation

HRID 453087 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7][O:8][C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14](SC)=[CH:13][CH:12]=1.[CH3:20]O>O>[CH3:7][O:8][C:9](=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([S:3]([CH3:20])(=[O:5])=[O:2])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12067662Methyl 2-(4-(methylthio)phenyl)acetateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 16640928Methyl 2-(4-(methylsulfonyl)phenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of oxone 30.7 g (50 mmol) was added drop by drop in 80 mL of water to a solution of 3.4 g (17.3 mmol) of the compound obtained in example 1 in 100 mL of methanol keeping the reaction in a water/ice bath. Once added, agitation continues for 5 h, allowing temperature to get room level. Then, part of the solvent is concentrated at reduced pressure and the precipitated solid is filtered washing with water repeatedly. After drying, this solid weighs 3 g. Waters from filtering are extracted with dichloromethane, the organic phase is washed with water, dried on sodium sulfate anhydride and concentrated in a rotary evaporator obtaining 1 more g of product than expected, yield 4 g (17 mmol, 100% yield). This solid melts with decomposition at 57° C. and its purity is 99% by HPLC. Spectroscopic data confirm the expected structure:

Workup

  1. customthe reaction in a water/ice bath
  2. additionOnce added
  3. customto get room level
  4. concentrationThen, part of the solvent is concentrated at reduced pressure
  5. filtrationthe precipitated solid is filtered
  6. washwashing with water repeatedly
  7. customAfter drying
  8. filtrationWaters from filtering
  9. extractionare extracted with dichloromethane
  10. washthe organic phase is washed with water
  11. customdried on sodium sulfate anhydride
  12. concentrationconcentrated in a rotary evaporator
  13. customobtaining 1 more g of product
  14. customat 57° C.

Sources & evidence

ORD record
ord-09cc3a2c8c824d6197ddce49d66513db
Source dataset
uspto-grants-2013_07
Patent number
US08492411B2

Reaction notes

Loading…