Nitric Acid → 2-(4-Hydroxy-3-nitrophenyl)-3-methylbutanoic acid

HRID 1447932

Reaction equation

HRID 1447932 reaction equation
[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1121922-(4-Hydroxyphenyl)-3-methylbutyric acid

Product 1

HCID 203433312-(4-Hydroxy-3-nitrophenyl)-3-methylbutanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of α-isopropyl-4-hydroxyphenylacetic acid (18.2 g, 0.094 mol) in acetic acid (130 ml) is heated to 40° C. and nitric acid (70%, 9.56 g, 0.095 mol) is added at such a rate that the reaction temperature is maintained at 38°-40° and never exceeded 45° C. The reaction mixture is stirred at 40°-42° C. overnight and poured into ice-water. The yellow solid is collected by filtration, washed and dried (19.1 g); m.p. 103°-105°.

Workup

  1. temperatureis maintained at 38°-40° and never exceeded 45° C
  2. filtrationThe yellow solid is collected by filtration
  3. washwashed
  4. customdried (19.1 g)

Sources & evidence

ORD record
ord-064d97781aa34826a40433985b9c75a6
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Linked notes

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