Potassium Permanganate → 5-(4-Cyanobenzyloxy)-2-nitrobenzoic acid

HRID 865347Notes

Reaction equation

HRID 865347 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[C:7]([C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:23]([O-:25])=[O:24])=[C:19]([CH:22]=2)[CH:20]=[O:21])=[CH:11][CH:10]=1)#[N:8]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.N1C=CC=CC=1>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:23]([O-:25])=[O:24])=[C:19]([CH:22]=2)[C:20]([OH:2])=[O:21])=[CH:26][CH:27]=1)#[N:8]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 229049735-(4-Cyanobenzyloxy)-2-nitrobenzaldehyde

Product 1

HCID 229049555-(4-Cyanobenzyloxy)-2-nitrobenzoic acidYield 125.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1049PyridineSolvent

Procedure

Potassium permanganate (6.18 g, 39.1 mmol) was added in portions to a stirred solution of 13.8 g (48.9 mmol) of 5-(4-cyanobenzyloxy)-2-nitrobenzaldehyde and 1.58 g (4.89 mmol) of tetrabutylammonium bromide in 70 mL of pyridine. After 1 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. Sodium hydrogen sulfite was added to destroy excess permanganate and the aqueous phase was separated and extracted with ethyl acetate. The combined organics were washed with 1N sodium hydrogen sulfate, brine, dried over anhydrous magnesium sulfate, and concentrated to give 14.6 g of 5-(4-cyanobenzyloxy)-2-nitrobenzoic acid as a powder, used without further purification. 1H NMR (300 MHz, d6 -acetone) d 8.07 (1H, d, J=8.8 Hz, O-Ar-H), 7.86 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.78 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.39 (1H, d, J=2.9 Hz, O-Ar-H), 7.36 (1H, dd, J=8.8, 2.9 Hz, O-Ar-H), 5.48 (2H, s, ArCH2O).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. additionSodium hydrogen sulfite was added
  4. customto destroy excess permanganate
  5. customthe aqueous phase was separated
  6. extractionextracted with ethyl acetate
  7. washThe combined organics were washed with 1N sodium hydrogen sulfate, brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-99a8a2453a5244a5a7d012ced83e14ed
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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