Nitric Acid → 4-Hydroxy-3-Nitroacetophenone

HRID 1108927Notes

Reaction equation

HRID 1108927 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][C:7]=1[OH:10])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 74694'-Hydroxyacetophenone

Product 1

HCID 1387234-Hydroxy-3-NitroacetophenoneYield 79.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5.00 g (36.7 ml) of 4-acetylphenol was dissolved in 50 ml of sulfuric acid. To the solution, 3.10 ml (40.7 mM) of nitric acid (60%, density=1.38) was gradually added dropwise under stirring at 2°-10° C. on an ice bath, followed by stirring at 2°-10° C. after the addition. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from methanol to obtain 5.84 g of 2-nitro-4-acetylphenol (Yield: 79.8%).

Workup

  1. stirringby stirring at 2°-10° C.
  2. additionafter the addition
  3. customAfter the reaction
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washwashed with water
  7. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-1da37e64f19341d187c9612d2c88fbf4
Source dataset
uspto-grants-1994_06
Patent number
US05318720

Reaction notes

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