Nitric Acid → 1-(5-(Benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

HRID 1662953Notes

Reaction equation

HRID 1662953 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([C:19](=[O:21])[CH3:20])[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[C:16]([OH:22])=[C:17]([C:19](=[O:21])[CH3:20])[CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 210728231-(5-(Benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18 mL fuming nitric acid are added dropwise to a solution of 81.5 g (0.34 mol) 1-(5-benzyloxy-2-hydroxyphenyl)-ethanone in 700 mL acetic acid while cooling with the ice bath, so that the temperature does not exceed 20° C. Then the reaction mixture is stirred for two hours at ambient temperature, poured onto ice water and filtered. The product is recrystallized from isopropanol, suction filtered and washed with isopropanol and diisopropylether. Yield: 69.6 g (72%); mass spectroscopy [M+H]+=288.

Workup

  1. customdoes not exceed 20° C
  2. additionpoured onto ice water
  3. filtrationfiltered
  4. customThe product is recrystallized from isopropanol, suction
  5. filtrationfiltered
  6. washwashed with isopropanol and diisopropylether

Sources & evidence

ORD record
ord-a1273b85820b445d9832cd1d392b8c87
Source dataset
uspto-grants-2011_10
Patent number
US08034809B2

Reaction notes

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