6-Oxabicyclo[3.1.0]hexane → 2-(4-Phenoxyphenoxy)cyclopentan-1-ol

HRID 46777

Reaction equation

HRID 46777 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[O:15]1[CH:17]2[CH2:18][CH2:19][CH2:20][CH:16]12.[OH-].[K+]>CCOCC.CCCCCC>[O:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:17]2[CH2:18][CH2:19][CH2:20][CH:16]2[OH:15])=[CH:10][CH:9]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 132544-PhenoxyphenolHCID 14797Potassium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 52 g of 4-hydroxydiphenyl ether and 23.5 g of 1,2-epoxycyclopentane is heated to 150° C. To this melt are added in the course of 25 minutes 6.7 g of 90% potassium hydroxide powder and the mixture is stirred for one hour at 130° C. After cooling, the reaction mixture is taken up in ether/hexane (1:1) and the organic solution is washed 4 times with 10% potassium hydroxide solution and 3 times with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated by rotary evaporation under reduced pressure. Distillation of the crude product yields 2-(4-phenoxyphenoxy)-cyclopentan-1-ol as a colourless oil with a boiling point of 181°-185° C./0.001 torr and a refractive index of nD20 =1.5812.

Workup

  1. temperatureAfter cooling
  2. washthe organic solution is washed 4 times with 10% potassium hydroxide solution and 3 times with saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by rotary evaporation under reduced pressure
  5. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-2e693e4050cb4b24ade852d15d1dcfb6
Source dataset
uspto-grants-1979_11
Patent number
US04175137

Linked notes

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