Nitric Acid → 3-Tert. butyl-5-nitro-6-methyl salicylic acid

HRID 1283941Notes

Reaction equation

HRID 1283941 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:7]([C:8]([OH:10])=[O:9])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[C:1]([C:5]1[CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]([CH3:14])=[C:7]([C:8]([OH:10])=[O:9])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 233613-tert-Butyl-6-methylsalicylic acid

Product 1

HCID 214831633-Tert. butyl-5-nitro-6-methyl salicylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

3-tert. Butyl-6-methyl salicylic acid (62.4 g 0.3M) was suspended in glacial acetic acid (300 ml) and cooled to 15°C. Concentrated nitric acid (22.5 ml) was added dropwise with stirring at such a rate that the temperature was maintained at approx. 10°-15°C. The mixture was stirred for 1 hour at this temp. and then poured onto crushed ice. A precipitate formed which was filtered off, washed with benzene and finally recrystallized from acetonitrile to give 3-tert. butyl-5-nitro-6-methyl salicylic acid (30.6 g) m.p. 225°-226°(dec)

Workup

  1. temperaturewas maintained at approx. 10°-15°C
  2. stirringThe mixture was stirred for 1 hour at this temp
  3. additionand then poured
  4. customonto crushed ice
  5. customA precipitate formed which
  6. filtrationwas filtered off
  7. washwashed with benzene
  8. customfinally recrystallized from acetonitrile

Sources & evidence

ORD record
ord-777cb25d87ae46e0958e530d7da8c8c6
Source dataset
uspto-grants-1976_08
Patent number
US03976777

Reaction notes

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