4-Nitrophenol → Benzene, 1-nitro-4-(phenylmethoxy)-

HRID 1696602Notes

Reaction equation

HRID 1696602 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 70842Benzene, 1-nitro-4-(phenylmethoxy)-Yield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-nitrophenol (10.0 g, 71.9 mmol), K2CO3 (19.9 g, 143.9 mmol) and KI (2.6 g, 15.8 mmol) in acetonitrile was added chloromethylbenzene (10.0 g, 79.1 mmol) at RT. The resultant mixture was heated to reflux for 3 h. After removal of the solvent, the residue was dissolved in EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to afford 4-benzyloxynitrobenzene (14.9 g, 90% yield). 1H NMR (400 MHz, CDCl3): δ 8.20 (d, J=8.0 Hz, 2H), 7.43-7.37 (m, 5H), 7.03 (d, J=8.0 Hz, 2H), 5.17 (s, 2H).

Workup

  1. temperatureto reflux for 3 h
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d8b7bda83b34bc29e6c6588ac65edb6
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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