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

HRID 1376650Notes

Reaction equation

HRID 1376650 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 (638 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-12e35c78fc3143d0b6be92e30a48ac4d
Source dataset
uspto-grants-1997_09
Patent number
US05663166

Reaction notes

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