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

HRID 46777

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-2e693e4050cb4b24ade852d15d1dcfb6
Quelldatensatz: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04175137

Verknüpfte Notizen

Wird geladen…