Water → HCID 22117695, compound

HRID 1275680Notes

Reaction equation

HRID 1275680 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][C:24]=1[N+:32]([O-:34])=[O:33].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][C:24]=2[N+:32]([O-:34])=[O:33])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 2407341-Chloro-4-ethoxy-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22117695HCID 22117695, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(benzyloxy)phenol (5.68 g, 28.4 mmol) in N,N-dimethylformamide (100 ml) was added potassium tert-butoxide (3.50 g, 31.2 mmol), and after stirring for 10 minutes, 1-chloro-4-ethoxy-2-nitrobenzene (5.73 g, 28.4 mmol) was added to the reaction solution, followed by stirring at 150° C. for 2 hours. The reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and after drying, the solvent was evaporated under reduced pressure. The resulting crude crystals were recrystallized from methanol to give 4-[4-(benzyloxy)phenoxy]-3-nitrophenetole (7.18 g).

Workup

  1. stirringby stirring at 150° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and after drying
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting crude crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-fdef1308958c40cea3a9fb63085e6a9b
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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