Potassium Carbonate → HCID 15541136, compound

HRID 1384972Notes

Reaction equation

HRID 1384972 reaction equation
[O:1]([CH2:9][C:10]([F:13])([F:12])[F:11])S(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:20]([O:23][C:24]1[C:29]([CH3:30])=[CH:28][C:27](O)=[CH:26][C:25]=1[CH3:32])(=[O:22])[CH3:21]>CC(=O)CC>[C:20]([O:23][C:24]1[C:29]([CH3:30])=[CH:28][C:27]([O:1][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:26][C:25]=1[CH3:32])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 10773702HCID 10773702, compound

Product 1

HCID 15541136HCID 15541136, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

2,2,2-Trifluoroethyl triflate (1.02 g, 4.40 mmol) and potassium carbonate (1.10 g, 1.01 mmol) were added to a solution of 4-hydroxy-2,6-dimethylphenyl acetate (673 mg, 3.73 mmol) in 2-butanone (15 mL). The mixture was stirred at 70° C. for 72 hours, then cooled to room temperature and concentrated. The residue was partitioned between water and ethyl acetate. The organic layer was washed twice with water and brine and dried. The solvent was removed in vacuo and the residue purified on silica gel, eluting with 10% ethyl acetate in hexanes, to give 2,6-dimethyl-4-(2,2,2-trifluoroethoxy)phenyl acetate (733 mg, 75%).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed twice with water and brine
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customthe residue purified on silica gel
  8. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ebeb631b6a93495ca9a98a24eac39c38
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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