Hydroxyphenylacetic acid → 4-Hydroxy-3-nitrophenylacetic acid

HRID 978237Notes

Reaction equation

HRID 978237 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].O>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 944Nitric AcidHCID 962Water

Product 1

HCID 4473644-Hydroxy-3-nitrophenylacetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydroxyphenylacetic acid (50 g, 0.32 m) in 300 ml of glacial acetic acid was cooled to 10° at which temperature 100 ml of nitric acid was slowly added. The mixture was allowed to reach room temperature, then was poured into 1 l of water. The separated solid was washed with water and recrystallized from ethanol to give 35 g of 4-hydroxy-3-nitrophenylacetic acid, m.p. 144°-146°.

Workup

  1. additionwas slowly added
  2. customto reach room temperature
  3. washThe separated solid was washed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-72156cc37c38435d992b59911f66baf0
Source dataset
uspto-grants-1987_05
Patent number
US04663482

Reaction notes

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