Potassium Hydroxide → HCID 53887396, compound

HRID 1872707Notes

Reaction equation

HRID 1872707 reaction equation
[C:1]([C:7]1[CH:8]=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=1)[CH2:12][OH:13])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[K+].[O-:19][Mn](=O)(=O)=O.[K+]>O1CCOCC1.O>[C:1]([C:7]1[CH:8]=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=1)[C:12]([OH:19])=[O:13])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 53836163HCID 53836163, compound

Product 1

HCID 53887396HCID 53887396, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Pivaloyl-2-methoxy benzyl alcohol (1.19 g, 5.35 mmol) was dissolved in dioxane (20 ml). A solution of KOH (0.449 g, 8.025 mmol in water (5 ml) was added followed by KMnO4 (1.69 g, 10.7 mmol). The mixture was allowed to stir at room temperature over the weekend. The solution was filtered through Celite and extracted with ether. The aqueous phase was acidified with dil. HCl and extracted with ether (3×50 ml). The organic layer was dried over magnesium sulphate and concentrated in vacuo to afford the title compound as a white solid (1.06 g).

Workup

  1. filtrationThe solution was filtered through Celite
  2. extractionextracted with ether
  3. extractionextracted with ether (3×50 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e182df00e2445c9bed88f28708f7d5f
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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