Potassium Permanganate → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid

HRID 1666589Notes

Reaction equation

HRID 1666589 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:20][Mn](=O)(=O)=O.[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][C:12]([C:13]([OH:20])=[O:14])=[CH:11][C:10]=1[CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 866393484-Benzyloxy-3-ethyl-5-methylbenzaldehyde

Product 1

HCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (5.6 g, 22.0 mmol) in acetone (150 mL), KMnO4 (4.52 g, 28.6 mmol) is added. The mixture becomes slightly warm (45° C.) and is stirred for 90 min at rt. The mixture is filtered and the filtrate is evaporated. The residue is treated with water and 10% aq. citric acid solution and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered, concentrated and dried under HV to give 4-benzyloxy-3-ethyl-5-methylbenzoic acid (4.38 g) as a white solid; LC-MS: tR=1.00 min, [M+1+CH3CN]+=312.09.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. additionThe residue is treated with water and 10% aq. citric acid solution
  4. extractionextracted twice with EA
  5. dry with materialextracts are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under HV

Sources & evidence

ORD record
ord-7a86d30e592b48e88b149a68f2f961a6
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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