Water → 4-Tert-butyl-2-nitrobenzoic acid

HRID 1916067Notes

Reaction equation

HRID 1916067 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#C)=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(#N)C.I(O)(=O)(=O)=[O:20].[OH2:24]>[Cl-].[Cl-].[Cl-].[Cl-].C.O.[Ru](Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:20])=[O:24])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 6342AcetonitrileHCID 65185Metaperiodic acidHCID 580162084-Tert-butyl-1-ethynyl-2-nitrobenzene

Product 1

HCID 2573264-Tert-butyl-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 18353858Carban tetrachlorideSolvent

Procedure

4-tert-Butyl-1-ethynyl-2-nitro-benzene (1.662 g, 8.176 mmol) was dissolved in 20 mL carban tetrachloride, 20 mL acetonitrile, and 40 mL water. Periodic acid (9.322 g, 40.89 mmol) was added followed by ruthenium(III)chloride hydrate (85 mg, 0.41 mmol). After stirring of 90 minutes, the resulting mixture was diluted with water and extracted with three portions of dichloromethane. The combined dichloromethane layers wee dried over anhydrous MgSO4, and concentrated in vacuo to yield 4-tert-Butyl-2-nitro-benzoic acid (1.924 g, 86.19 mmol).

Workup

  1. extractionextracted with three portions of dichloromethane
  2. dry with materialThe combined dichloromethane layers wee dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18d0a3a9c86547049fad70b4406d3d1e
Source dataset
uspto-grants-2013_12
Patent number
US08618098B2

Reaction notes

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