Acetone → HCID 13037175, compound

HRID 1759254Notes

Reaction equation

HRID 1759254 reaction equation
CC(C)=O.[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([OH:24])=[C:17]([CH:23]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:37][C:38]([F:41])([F:40])[F:39])(=O)=O>O.C(OCC)C>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([O:24][CH2:37][C:38]([F:41])([F:40])[F:39])=[C:17]([CH:23]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 13037174HCID 13037174, compound

Product 1

HCID 13037175HCID 13037175, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a refluxing mixture of 100 ml of acetone, 10.3 g (0.0379 mole) of ethyl 5-benzyloxy-2-hydroxybenzoate and 10.5 g (0.0757 mole) of potassium carbonate is added dropwise over about 1 hour 13.2 g (0.0568 mole) 2,2,2-trifluoroethyl trifluoromethanesulfonate. The mixture is heated at reflux for another 16 hours then evaporated to provide a residue which is dissolved in water and diethyl ether. The layers are separated and the ether is washed with water, then saturated sodium chloride solution and dried over magnesium sulfate. The magnesium sulfate is removed by filtration and the diethyl ether is removed by evaporation to provide the product, ethyl 5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzoate. The infrared spectrum of this material is consistent with the assigned structure.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for another 16 hours
  3. customthen evaporated
  4. customto provide a residue which
  5. customThe layers are separated
  6. washthe ether is washed with water
  7. dry with materialsaturated sodium chloride solution and dried over magnesium sulfate
  8. customThe magnesium sulfate is removed by filtration
  9. customthe diethyl ether is removed by evaporation

Sources & evidence

ORD record
ord-de8d666c57a24f0181ae5ba10b9ddd79
Source dataset
uspto-grants-1982_07
Patent number
US04339587

Reaction notes

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