Phenol → Ethyl 5-phenoxypentanoate

HRID 1059485Notes

Reaction equation

HRID 1059485 reaction equation
[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16]([O:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23]Br)[CH3:17]>CC(C)=O>[CH2:16]([O:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][O:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:17]

Participants

6

Reactant 4

HCID 996PhenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 582195Ethyl 5-phenoxypentanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Dehydrated acetone of 240 ml was put in a 3-necked round-bottom flask, potassium iodide (0.06 mol), potassium carbonate (0.11 mol), and phenol (0.07 mol) were added to stir sufficiently. In this solution, 5-bromo valeric acid ethyl ester (0.06 mol) was dropped in a nitrogen atmosphere and refluxed at 60±5° C. to react for 24 hours. After completion of the reaction, a reaction solution was exsiccated to condensation using an evaporator, and dissolved again in methylene chloride, and water was added to the solution to separate and an organic layer was dehydrated by using magnesium sulfate anhydride followed by exsiccation for condensation using the evaporator. Hot methanol was added to a dried matter (reactant) yielded to dissolve and cooled slowly to precipitate again, resulting in a yield of 5-phenoxy valeric acid ethyl ester (PxVA). At this point, the yield ratio of this ester to 5-bromo valeric acid ethyl ester was 72 mol %.

Workup

  1. customto react for 24 hours
  2. customAfter completion of the reaction
  3. customa reaction solution was exsiccated to condensation
  4. customan evaporator
  5. dissolutiondissolved again in methylene chloride
  6. additionwater was added to the solution
  7. customto separate
  8. customfollowed by exsiccation for condensation
  9. customthe evaporator
  10. additionHot methanol was added to a dried matter (reactant)
  11. customyielded
  12. dissolutionto dissolve
  13. temperaturecooled slowly
  14. customto precipitate again

Sources & evidence

ORD record
ord-9b936323000149a798aba61ed3eda898
Source dataset
uspto-grants-2003_02
Patent number
US06521429B2

Reaction notes

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