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

HRID 33374Notes

Reaction equation

HRID 33374 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 of fuming nitric acid are added dropwise to a solution of 81.5 g (0.34 mol) 1-(5-benzyloxy-2-hydroxy-phenyl)-ethanone (known from U.S. Pat. No. 4,460,581) in 700 mL acetic acid, while cooling with the ice bath, such 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 recrystallised 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 recrystallised from isopropanol, suction
  5. filtrationfiltered
  6. washwashed with isopropanol and diisopropylether

Sources & evidence

ORD record
ord-4d36b79c31544837887e5a5a6b1552df
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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