Potassium Hydroxide → 2-(4-Phenoxyphenoxy)cyclopentan-1-ol

HRID 46779Notes

Reaction equation

HRID 46779 reaction equation
[OH-].[K+].C([O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=O)C>O.C(O)C>[O:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:8]2[CH2:9][CH2:10][CH2:11][CH:7]2[OH:6])=[CH:14][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 203857491-Acetoxy-2-(4-phenoxyphenoxy)-cyclopentane

Product 1

HCID 222476762-(4-Phenoxyphenoxy)cyclopentan-1-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.68 g of potassium hydroxide in 20 ml of water is added at room temperature to a solution of 6.24 g of 1-acetoxy-2-(4-phenoxyphenoxy)-cyclopentane in 50 ml of ethanol. The mixture is then refluxed for 3 hours and, after cooling, concentrated to 166 of its original volume by rotary evaporation. The residue is poured into ice-water. After extraction with ether, the organic phase is washed three times with saturated sodium chloride solution, dried over sodium sulphate and concentrated by rotary evaporation. Distillation of the residue yields 2-(4-phenoxyphenoxy)-cyclopentan-1-ol as a colourless oil with a boiling point of 181°-185° C./0.001 torr.

Workup

  1. temperatureThe mixture is then refluxed for 3 hours
  2. temperatureafter cooling
  3. concentrationconcentrated to 166 of its original volume by rotary evaporation
  4. additionThe residue is poured into ice-water
  5. extractionAfter extraction with ether
  6. washthe organic phase is washed three times with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by rotary evaporation
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-f0616c2b746642858f6b65dc1ecff7f3
Source dataset
uspto-grants-1979_11
Patent number
US04175137

Reaction notes

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