Benzyl Bromide → 1,2-Bis(benzyloxy)-4-nitrobenzene

HRID 19982Notes

Reaction equation

HRID 19982 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1O.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[O:4][CH2:1][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 35051094-Nitrocatechol

Product 1

HCID 127366801,2-Bis(benzyloxy)-4-nitrobenzeneYield 141.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (4.14 g; 30 mmol) was added to a solution of 3,4-dihydroxy-1-nitrobenzene (1.55 g; 10 mmol) and benzyl bromide (3.42 g; 20 mmol) in acetone (100 ml). The reaction mixture was refluxed for 12 hours. After the removal of the solvent under reduced pressure, the residue was partitioned between ethyl acetate (150 ml) and water (50 ml). The ethyl acetate layer was washed with water (100 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 2.37 g of 3,4-Dibenzyloxy-1-nitro benzene. (Yield=70%)

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. customAfter the removal of the solvent under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (150 ml) and water (50 ml)
  4. washThe ethyl acetate layer was washed with water (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d7d914f2e3d241808109d04e19eed901
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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