Phenol → 6-(Benzyloxy)-2-phenoxyquinoline

HRID 1869795Notes

Reaction equation

HRID 1869795 reaction equation
[OH-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23](Cl)[CH:22]=[CH:21]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([N+](CCCC)(CCCC)CCCC)CCC>O.C1(C)C=CC=CC=1>[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:22]=[CH:21]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 16028TetrabutylammoniumHCID 112194246-(Benzyloxy)-2-chloroquinoline

Product 1

HCID 117717826-(Benzyloxy)-2-phenoxyquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a 50% (w/w) NaOH solution (10.2 ml) is added phenol (0.697 g). After 50 minutes at room temperature, toluene (10.21 ml) and 6-(benzyloxy)-2-chloroquinoline 12 (2 g) and tetrabutyl ammonium (2.062 g) are added. The solution is stirred under argon at reflux for 24 h. Water (5 ml) is added and the solution is extracted with toluene (3×10 ml). The organic phases are dried over MgSO4 and evaporated under vacuum. The residue is purified by silica gel chromatography using AcOEt/cyclohexane 20/80 as eluent. The obtained solid is dissolved in AcOEt and pentane is added; 6-(benzyloxy)-2-phenoxyquinoline 13 precipitates as a white powder.

Workup

  1. temperatureat reflux for 24 h
  2. extractionthe solution is extracted with toluene (3×10 ml)
  3. dry with materialThe organic phases are dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue is purified by silica gel chromatography
  6. dissolutionThe obtained solid is dissolved in AcOEt
  7. additionpentane is added
  8. custom6-(benzyloxy)-2-phenoxyquinoline 13 precipitates as a white powder

Sources & evidence

ORD record
ord-9fcfcab1d533481586d817cb4514b5a2
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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