Potassium Hydroxide → 54378-87-9

HRID 345106Notes

Reaction equation

HRID 345106 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-733f6eee3bea450a9a3f2333a189046e
Source dataset
uspto-grants-1991_10
Patent number
US05055450

Reaction notes

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