Phenol → Diphenyl Ether

HRID 1907896Notes

Reaction equation

HRID 1907896 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](C23NCCN2C(=O)C2C3=CC=CC=2)=[CH:4][CH:3]=1.F[C:22]1[CH:30]=[CH:29][C:25](C(Cl)=O)=[CH:24][CH:23]=1.C1(O)C=CC=CC=1.ClCC#N.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:22]1([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:30]=[CH:29][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 996PhenolHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 678794-Fluorobenzoyl chlorideHCID 346194513450-05-0

Product 1

HCID 7583Diphenyl Ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 239 was prepared from 9b-(4-hydroxyphenyl)-1,2,3,9b-tetrahydroimidazo[2,1-a]isoindol-5-one using Method L. The tetrahydroimidazoisoindolone was bis-acylated with 4-fluorobenzoyl chloride according to Method H and the resulting phenolic ester function was converted to a phenol by basic hydrolysis. The product was then treated with chloroacetonitrile and K2CO3 in acetone and heated to reflux for 30 h to yield phenyl ether compound 239.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 h

Sources & evidence

ORD record
ord-ca046bd3064643f99cfd1b5331b2c8d1
Source dataset
uspto-grants-2013_12
Patent number
US08598193B2

Reaction notes

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