3-Phenoxyphenol → HCID 18696603, compound

HRID 1870554Notes

Reaction equation

HRID 1870554 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][N:23]=1>O1CCCC1>[N+:28]([C:27]1[C:22]([O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)=[N:23][CH:24]=[CH:25][CH:26]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 128423-PhenoxyphenolHCID 796132-Chloro-3-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18696603HCID 18696603, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Phenoxyphenol (3 g, 16.1 mmol) was added to a solution of potassium t-butoxide (1.90 g of 90%, 16.6 mmol) in 50 mL of dry tetrahydrofuran at room temperature after which the reaction was stirred at room temperature for 10 min. Then, 2-chloro-3-nitropyridine (2.56 g, 16.1 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water, extracted twice with methylene chloride and dried over magnesium sulfate. The solvent was then removed to yield the title compound of Step A as an oil. 1H NMR (CDCl3 ; 300 MHz): δ 6.85 (m,1H), 6.90 (m,2H), 7.0-7.2 (m,4H), 7.3-7.4 (m,3H), 8.35 (m,2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted twice with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was then removed

Sources & evidence

ORD record
ord-780f50016f414e4d816d4b636f3f798d
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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