Nitric Acid → 5-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid

HRID 1787459Notes

Reaction equation

HRID 1787459 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[C:12]([C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 70103155-Tert-Butyl-2-Methoxybenzoic Acid

Product 1

HCID 508823195-(Tert-butyl)-2-methoxy-3-nitrobenzoic acidYield 54.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a suspension of 2.10 g (10.1 mmol) of 2-methoxy-5-tert-butylbenzoic acid in 6 mL of conc H2SO4 cooled in an ice bath was added dropwise a solution of 1 mL (11.1 mmol) of HNO3 in 2 ml H2SO4. The mixture was stirred, warming from 0° C. to rt over 3 h. The mixture was then poured into crushed ice and the resulting precipitate was filtered and dried. Recrystallization from 1:1 water/EtOH (8 mL/g) provided 1.4 g of product Intermediate 10.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturewarming from 0° C. to rt over 3 h
  3. additionThe mixture was then poured
  4. custominto crushed ice
  5. filtrationthe resulting precipitate was filtered
  6. customdried
  7. customRecrystallization from 1:1 water/EtOH (8 mL/g)

Sources & evidence

ORD record
ord-f9bb8e990ce042e5b0b296af5602bee1
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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