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

HRID 280825Notes

Reaction equation

HRID 280825 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

Fumic 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 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 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 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-8a9daf0394e04afeaa709e6b74547b9f
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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