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

HRID 1844615Notes

Reaction equation

HRID 1844615 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])([CH3:8])([CH3:7])[CH3:6]>S(=O)(=O)(O)O>[C:5]([C:9]1[CH:10]=[C:11]([N+:1]([O-:4])=[O:2])[C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

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

Product 1

HCID 508823195-(Tert-butyl)-2-methoxy-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of 2.3 ml 65% nitric acid and 2.6 ml 96% sulphuric acid is added dropwise to an ice-cooled solution of 5.00 g 5-tert-butyl-2-methoxy-benzoic acid in 15 ml 96% sulphuric acid. The solution is stirred for 1.5 h in the cooling bath and then for 1 h at ambient temperature. Then the solution is added to ice water, and the precipitate formed is filtered off and taken up in dichloromethane. The dichloromethane phase is dried (Na2SO4), and the solvent is eliminated completely.

Workup

  1. waitfor 1 h at ambient temperature
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. dry with materialThe dichloromethane phase is dried (Na2SO4)

Sources & evidence

ORD record
ord-84470b09dfc340a59eaa40743f48fe97
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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