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

HRID 1958792Notes

Reaction equation

HRID 1958792 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 2N 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 as a pale yellow solid (19.2 g). LC-MS: tR=1.00 min; 1H NMR (D6-DMSO): δ 1.13-1.22 (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 (br s, 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-2dcba85d2afb401081c984225ddbd61d
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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