Hydroxyphenylacetic acid → 4-Hydroxy-3-nitrophenylacetic acid

HRID 1766008Notes

Reaction equation

HRID 1766008 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1.O>C(O)(=O)C>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 944Nitric AcidHCID 962Water

Product 1

HCID 4473644-Hydroxy-3-nitrophenylacetic acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of nitric acid (24.5 ml, 398 mmol) in acetic acid (20 ml) was slowly added dropwise under cooling with ice-bath to a solution of (4-hydroxyphenyl)acetic acid (50.4 g, 330 mmol) in acetic acid (230 ml) such that the temperature of the reaction solution did not exceed 10° C. After the reaction solution was stirred for 2 hours, water (1 L) was added dropwise thereto and the precipitated crystals were collected by filtration. The resultant crystals were washed with water and dried, whereby (4-hydroxy-3-nitrophenyl)acetic acid (49 g) was obtained as crystals with a mp of 144 to 146° C.

Workup

  1. customdid not exceed 10° C
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe resultant crystals were washed with water
  4. customdried

Sources & evidence

ORD record
ord-b5e6fbb9539f497eba3224d487107bb3
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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