Ethylparaben → Ethyl 4-(4,4,4-trifluorobutoxy)benzoate

HRID 339512Notes

Reaction equation

HRID 339512 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.I[CH2:14][CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18].C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C>[F:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 27751891,1,1-Trifluoro-4-iodobutane

Product 1

HCID 15285933Ethyl 4-(4,4,4-trifluorobutoxy)benzoateYield 87%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of ethyl 4-hydroxybenzoate (0.46 g, 2.80 mmol), 1-iodo-4,4,4-trifluorobutane (0.67 g, 2.80 mmol) and anhydrous K2CO3 (1.16 g, 8.40 mmol) in methyl ethyl ketone (5 ml) was heated under reflux for 4 h under an atmosphere of argon. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was partitioned between water (15 ml) and Et2O (30 ml). The organic layer was separated, and the aqueous phase extracted with Et2O (2×20 ml). The combined organic extracts were washed with brine (15 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was purified by flash chromatography (3:1 Hexane/EtOAc) to give the title compound (0.67 g, 87%) as a colourless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h under an atmosphere of argon
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was partitioned between water (15 ml) and Et2O (30 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous phase extracted with Et2O (2×20 ml)
  7. washThe combined organic extracts were washed with brine (15 ml)
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed under reduced pressure
  10. customto give a solid which
  11. customwas purified by flash chromatography (3:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-66d276ea25c54e53ad6537537d74cf13
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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