Potassium Hydroxide → 54378-87-9

HRID 1165522Notes

Reaction equation

HRID 1165522 reaction equation
[C:1]1([C:11]([O:13]CC)=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CCO>[CH2:9]([O:8][C:6]([C:1]1([C:11]([OH:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 77830Diethyl 1,1-cyclopentanedicarboxylate

Product 1

HCID 5431323854378-87-9Yield 0.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of diethyl 1,1-cyclopentane dicarboxylate (2.5 g, 11.68 mol) in EtOH (10 ml) was added dropwise a solution of KOH (654 mg, 11.68 mmol) in EtOH (10 ml) over 1/2 hour. The resulting mixture was stirred at room temperature for 96 hr, concentrated under vacuum, and partitioned between H2O and EtOAc. The aqueous layer was acidified with concentrated HCl and extracted with EtOAc. The EtOAc extracts were washed (brine), dried (Na2SO4), filtered, and concentrated under vacuum to give the product (1.73 g) as a clear oil.

Workup

  1. concentrationconcentrated under vacuum
  2. custompartitioned between H2O and EtOAc
  3. extractionextracted with EtOAc
  4. washThe EtOAc extracts were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-62f287fc60864de192b7813d885fa3cc
Source dataset
uspto-grants-1990_03
Patent number
US04910190

Reaction notes

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