Water → Cyclopentanecarboxylic acid, 2,2,5,5-tetramethyl-

HRID 231728Notes

Reaction equation

HRID 231728 reaction equation
[CH:1]([CH:3]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C:4]1([CH3:11])[CH3:10])=[O:2].CC(C)=[O:14].OS(O)(=O)=O.O=[Cr](=O)=O.O.C(OCC)(=O)C>CC(C)=O.C(O)(C)C>[CH3:8][C:7]1([CH3:9])[CH2:6][CH2:5][C:4]([CH3:11])([CH3:10])[CH:3]1[C:1]([OH:14])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9793878Cyclopentanecarboxaldehyde, 2,2,5,5-tetramethyl-HCID 131709961Jones' reagent

Product 1

HCID 10197889Cyclopentanecarboxylic acid, 2,2,5,5-tetramethyl-Yield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

2.47 g of 1-formyl-2,2,5,5-tetramethylcyclopentane was dissolved in 26 ml of acetone, and 5.2 ml of Jones' reagent was added thereto with ice cooling. After stirring at room temperature for 4 hours, 26 ml of water, 26 ml of ethyl acetate and 2.6 ml of isopropyl alcohol were added thereto, and the mixture was stirred at room temperature for 30 minutes, and the resulting layers were separated. The organic layer was washed with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and subjected to filtration. The filtrate was concentrated under reduced pressure, whereby 2.51 g of 2,2,5,5-tetramethylcyclopentanecarboxylic acid was obtained. Yield 92%.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customthe resulting layers were separated
  3. washThe organic layer was washed with water and aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationsubjected to filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cab7867f585e4dd0a363ab331acaafeb
Source dataset
uspto-grants-1989_07
Patent number
US04847390

Reaction notes

Loading…