Acetone → 2-Methyl-4-methoxy-5-nitrophenyl mesylate

HRID 1029992Notes

Reaction equation

HRID 1029992 reaction equation
[CH3:1]C(C)=O.[S:5]([O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([OH:19])=[CH:12][C:11]=1[CH3:20])(=[O:8])(=[O:7])[CH3:6].C(=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O>O>[S:5]([O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([O:19][CH3:1])=[CH:12][C:11]=1[CH3:20])(=[O:7])(=[O:8])[CH3:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 198211444-Hydroxy-2-methyl-5-nitrophenyl methanesulfonate

Product 1

HCID 198211562-Methyl-4-methoxy-5-nitrophenyl mesylateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml of acetone, were added 19.1 g (77.3 mmol) of 2-methyl-4-hydroxy-5-nitrophenyl mesylate, 31.2 g of sodium carbonate and 19.2 g of dimethyl sulfate. The obtained mixture was heated under reflux for 3 hours. The reaction mixture was cooled and 700 ml of water was poured thereto. Then the mixture was extracted with 700 ml of chloroform, and the extract was washed with water and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, the residue was recrystallized from a solvent mixture (hexane/acetone (2:1, by volume)) to thereby give 15.4 g (59.1 mmol) of 2-methyl-4-methoxy-5-nitropheyl mesylate. The yield was 77%.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionThen the mixture was extracted with 700 ml of chloroform
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous Glauber's salt
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe residue was recrystallized from a solvent mixture (hexane/acetone (2:1, by volume))

Sources & evidence

ORD record
ord-a5742835df71442794140db348dd210e
Source dataset
uspto-grants-1992_04
Patent number
US05104414

Reaction notes

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