Nitric Acid → 4-(Benzyloxy)-2-nitrophenol

HRID 979439Notes

Reaction equation

HRID 979439 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OC(=O)C)C>[N+:1]([C:15]1[CH:14]=[C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:18]=[CH:17][C:16]=1[OH:19])([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7638Monobenzone

Product 1

HCID 46066344-(Benzyloxy)-2-nitrophenolYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Fuming nitric acid (d=1.52, 43.6 g, 0.70 mole) was dropwise added under stirring to 4-benzyloxyphenol (138.0 g, 0.69 mole) in ethylacetate (500 ml) at 0° C. The resulting solution was raised at room temperature and then washed in a separatory funnel with sodium hydrogen carbonate in water (saturated solution). The organic layer was separated and evaporated under vacuum and the residual solid was crystallized from methanol (100 ml) to give the nitrophenol (yield of (a): 62.54 g, 36%) as yellow prisms. The product structure was confirmed by NMR and IR spectra.

Workup

  1. washwashed in a separatory funnel with sodium hydrogen carbonate in water (saturated solution)
  2. customThe organic layer was separated
  3. customevaporated under vacuum
  4. customthe residual solid was crystallized from methanol (100 ml)

Sources & evidence

ORD record
ord-02e05fa34e224d79ac18329ddc3fbdd7
Source dataset
uspto-grants-1987_05
Patent number
US04668610

Reaction notes

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