Nitric Acid → HCID 21459099, compound

HRID 2260215Notes

Reaction equation

HRID 2260215 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[CH:8][C:7]=1[O:17][CH3:18]>C(O)(=O)C>[OH:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[CH:8][C:7]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 140350981-(4-Hydroxy-3-methoxyphenyl)butan-1-one

Product 1

HCID 21459099HCID 21459099, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.5 ml of 11.2N nitric acid are added dropwise to a solution of 12.7 g of 4'-hydroxy-3'-methoxybutyrophenone in 250 ml of glacial acetic acid while stirring within 10 minutes. The reaction mixture is subsequently stirred for 15 minutes, poured into ice-water, the separated precipitate is filtered under suction, washed with ice-water and taken up in methylene chloride. The methylene chloride solution is filtered over 50 g of silica gel. The material obtained is recrystallized from methylene chloride/n-hexane. There is obtained 4'-hydroxy-3'-methoxy-5'-nitrobutyrophenone in the form of yellow crystals of m.p. 92°-93°.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 15 minutes
  2. filtrationthe separated precipitate is filtered under suction
  3. washwashed with ice-water
  4. filtrationThe methylene chloride solution is filtered over 50 g of silica gel
  5. customThe material obtained
  6. customis recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-5b3e1f12453c43ec9369ca6b9b2ef1d8
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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