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

HRID 2037344Notes

Reaction equation

HRID 2037344 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 72.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (25.0 g, 98.3 mmol) in acetone (500 mL), KMnO4 (20.2 g, 127.8 mmol) is added. The mixture becomes warm (45° C.). The mixture is stirred at rt for 16 h before it is filtered over glass filters. The clear, colourless filtrate is concentrated, diluted with water and acidified with 2 N aq. HCl, then extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered concentrated and dried to give 4-benzyloxy-3-ethyl-5-methyl-benzoic acid (19.2 g) as a pale yellow solid; LC-MS: tR=1.00 min; 1H NMR (D6-DMSO): δ1.13-1.22 (m, 3H), 2.32 (s, 3H), 2.64-2.72 (m, 2H), 4.87 (s, 2H), 7.34-7.56 (m, 5H), 7.69 (m, 2H), 12.66 (s br, 1H).

Workup

  1. filtrationis filtered over glass filters
  2. concentrationThe clear, colourless filtrate is concentrated
  3. additiondiluted with water
  4. extractionextracted twice with EA
  5. dry with materialextracts are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-4daf1f7edcc24a2db00dc151ff6df762
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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