Diethyl Ether → HCID 21958895, compound

HRID 1767723Notes

Reaction equation

HRID 1767723 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:18][CH2:19][CH3:20])(=[O:17])[C:8]1[CH:16]=[CH:15][C:13]([OH:14])=[C:10]([O:11][CH3:12])[CH:9]=1.CS(O[CH2:26][C:27]([F:30])([F:29])[F:28])(=O)=O.C(OCC)C>CN(C)C=O>[F:28][C:27]([F:30])([F:29])[CH2:26][O:14][C:13]1[CH:15]=[CH:16][C:8]([C:7]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 5565652,2,2-Trifluoroethyl Methanesulfonate

Product 1

HCID 21958895HCID 21958895, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (62.2 g, 450 mmol) was added to a solution of ethyl vanillate (58.9 g, 300 mmol) in dimethylformamide (400 ml) and the reaction heated to 120° C. 2,2,2-Trifluoroethyl methanesulphonate (63.4 g, 360 mmol) was added over 15 minutes and the reaction heated at 120° C. for 15 hours. The reaction was cooled to ambient temperature, diethyl ether (400 ml) was added and the reaction was filtered. The filtrate was evaporated in vacuo and the residue was taken up in a mixture of diethyl ether (375 ml) and isohexane (375 ml). The organic layer was concentrated in vacuo to a total volume of 250 ml and the solid which crystallised out was collected by suction filtration. Drying of the solid in vacuo yielded ethyl 4-(2,2,2-trifluoroethoxy)-3-methoxybenzoate (43.0 g, 52% yield) as a white crystalline solid:

Workup

  1. temperaturethe reaction heated at 120° C. for 15 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. filtrationthe reaction was filtered
  4. customThe filtrate was evaporated in vacuo
  5. additionthe residue was taken up in a mixture of diethyl ether (375 ml) and isohexane (375 ml)
  6. concentrationThe organic layer was concentrated in vacuo to a total volume of 250 ml
  7. customthe solid which crystallised out
  8. filtrationwas collected by suction filtration
  9. customDrying of the solid in vacuo

Sources & evidence

ORD record
ord-f5d1d8ad47334ce688425997f254b115
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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