Dimethyl Sulfate → HCID 57419449, compound

HRID 876112Notes

Reaction equation

HRID 876112 reaction equation
[C:1]([C:5]1[C:6]([OH:18])=[C:7]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[C:1]([C:5]1[C:6]([O:18][CH3:19])=[C:7]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 11097093HCID 11097093, compound

Product 1

HCID 57419449HCID 57419449, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-tert-butyl-2-hydroxy-5-nitrobenzoate (11.41 g, 45.0 mmol), potassium carbonate (9.34 g, 67.6 mmol), acetone (200 mL), and dimethyl sulfate (6.46 g, 67.6 mmol) were added together. The resultant mixture was then heated to reflux for 16 h. The mixture was then filtered and the solid was washed with ethyl acetate. The resulting organic liquid was then concentrated under vacuum to an oil and redissolved in ethyl acetate (600 mL). The organic solution was then washed with water, dried, filtered and concentrated under vacuum to an oil that was then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes) to yield the title compound as an oil (10.42, 87%).

Workup

  1. temperatureto reflux for 16 h
  2. filtrationThe mixture was then filtered
  3. washthe solid was washed with ethyl acetate
  4. concentrationThe resulting organic liquid was then concentrated under vacuum to an oil
  5. dissolutionredissolved in ethyl acetate (600 mL)
  6. washThe organic solution was then washed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum to an oil that
  10. customwas then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6417fe2f90334377a8dbea403e7422c1
Source dataset
uspto-grants-2015_03
Patent number
US08986740B2

Reaction notes

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