Nitric Acid → 1-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone

HRID 1195943Notes

Reaction equation

HRID 1195943 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[O:15][CH3:16]>O>[OH:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2214Acetovanillone

Product 1

HCID 2947641-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing 40 ml of nitric acid (d=1.41) and 40 ml of water was gradually added while cooling (below 7° C.) and stirring 25.0 g of 4'-hydroxy-3'-methoxyacetophenone. After stirring for 0.5 h at 0° C. the product was filtered, washed first with diluted nitric acid (1:1) and then with water. Yield 24.0 g (75%). The 1H-NMR-spectrum of the product was in accordance with the structure alleged.

Workup

  1. additionwas gradually added
  2. temperaturewhile cooling (below 7° C.)
  3. filtrationwas filtered
  4. washwashed first with diluted nitric acid (1:1)

Sources & evidence

ORD record
ord-0d6fa06d5ebb4065b9a1c625cb7077fd
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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