4-Hydroxybiphenyl → 1-(Biphenyl-4-yloxy)-2,3-epoxypropane

HRID 638036Notes

Reaction equation

HRID 638036 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>>[O:24]1[CH2:23][CH:22]1[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 71034-HydroxybiphenylHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 1073251-(Biphenyl-4-yloxy)-2,3-epoxypropane

Procedure

A suspension of 10 g of 4-hydroxybiphenyl and 10 g of pulverised potassium carbonate in 75 ml of epichlorohydrin is stirred under reflux from 4 hours. The reaction mixture is concentrated by evaporation, water is added to the residue and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated by evaporation. The residue is recrystallised from isopropanol, yielding 4-(2,3-epoxypropoxy)-biphenyl having a melting point of 86°-88°.

Workup

  1. temperatureunder reflux from 4 hours
  2. concentrationThe reaction mixture is concentrated by evaporation, water
  3. additionis added to the residue
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customThe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-f8f1f25a485f4b769912f6e254c15468
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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