Water → Methyl 2,6-dimethylbenzoate

HRID 453861Notes

Reaction equation

HRID 453861 reaction equation
C([O-])([O-])=O.[K+].[K+].S([O:12][CH3:13])(OC)(=O)=O.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17](O)=[O:18].O>C(OCC)(=O)C>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17]([O:12][CH3:13])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 124392,6-Dimethylbenzoic acid

Product 1

HCID 519028Methyl 2,6-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (10.1 mmol, 1.5 equiv.) and dimethyl sulfate (7.4 mmol, 1.1 equiv.) were added at 25° C. to a solution of 2,6-dimethylbenzoic acid (6.7 mmol, 1 equiv.), and the mixture was stirred for 1 h. The solvent was reduced under reduced pressure, the residue was taken up in ethyl acetate (100 ml), and water (20 ml) was added. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with sat. NaCl solution, dried over Na2SO4 and concentrated under reduced pressure. The crude product was used in the next stage without being purified further. Yield: quantitative

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic phases were washed with sat. NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customwithout being purified further

Sources & evidence

ORD record
ord-65a8247fc88044e58887222e3f7b51ff
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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