Water → 2-cyclobutyl-2-hydroxy-2-phenylacetic acid

HRID 1107394Notes

Reaction equation

HRID 1107394 reaction equation
[CH:1]1([C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[C:6]#C)[CH2:4][CH2:3][CH2:2]1.[Mn]([O-])(=O)(=O)=[O:16].[K+].S([O-])([O-])=O.[Na+].[Na+].[OH2:27]>>[CH:1]1([C:5]([OH:8])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([OH:16])=[O:27])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 15030052HCID 15030052, compound2×

Product 1

HCID 108890462-cyclobutyl-2-hydroxy-2-phenylacetic acidYield 36.8%

Procedure

To 1-cyclobutyl-1-phenyl-2-propin-1-ol (Compound (10), 5.80 g), water (20 ml) was added. Under stirring, an aqueous solution (300 ml) of potassium permanganate (14.0 g) was added dropwise to the resulting mixture at 0° C., followed by vigorous stirring for further 2 hours. Sodium sulfite was added to the reaction mixture at room temperature. The precipitate so obtained was filtered through Celite and the filtrate was extracted with ether. The organic layer was dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain the title compound (2.36 g, 36.8%)) as colorless prism.

Workup

  1. stirringby vigorous stirring for further 2 hours
  2. customThe precipitate so obtained
  3. filtrationwas filtered through Celite
  4. extractionthe filtrate was extracted with ether
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was then removed under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4f5ee957953e477b9e62818f4f7ef8e3
Source dataset
uspto-grants-2000_05
Patent number
US06060485

Reaction notes

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