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

HRID 1090698Notes

Reaction equation

HRID 1090698 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:16]([O-])([OH:18])=[O:17].O>C(O)(=O)C>[N+:16]([C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]=[CH:13][C:12]=1[OH:15])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 7638Monobenzone

Product 1

HCID 46066344-(Benzyloxy)-2-nitrophenolYield 70.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 20 g (0.1 mole) of 4-phenylmethoxy-phenol in 200 ml acetic acid were added, dropwise at room temperature, 7.26 ml of nitric acid (d=1.4, 0.105 mole). 2 Hours after completion of the addition the reaction medium was poured onto cold water and extracted twice with 250 ml of methylene chloride. The organic phase was washed twice with 200 ml of water and dried over sodium sulfate. Then the solvent was evaporated and the residue flash chromatographed using ethyl acetate/heptane 30/70 as eluting solvent to give 17.3 g (Yield=70.6%) of 2-nitro-4-phenylmethoxy-phenol.

Workup

  1. addition2 Hours after completion of the addition the reaction medium
  2. extractionextracted twice with 250 ml of methylene chloride
  3. washThe organic phase was washed twice with 200 ml of water
  4. dry with materialdried over sodium sulfate
  5. customThen the solvent was evaporated
  6. customthe residue flash chromatographed
  7. washas eluting solvent

Sources & evidence

ORD record
ord-a6ff07afc1814b618a4d96cfc1f3d9d7
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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