Potassium Hydroxide → 54378-87-9

HRID 1613888Notes

Reaction equation

HRID 1613888 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 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of diethyl 1,1-cyclopentane dicarboxylate (2.5 g, 11.68 mmol) 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-1083fc1cf9874227b3b9db5c3a5d8b5b
Source dataset
uspto-grants-1993_03
Patent number
US05194588

Reaction notes

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