Potassium Hydroxide → HCID 18317887, compound

HRID 1966076Notes

Reaction equation

HRID 1966076 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:10]([O:12]C)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[K+]>CO>[CH3:1][O:2][C:3]([C:5]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12609605Dimethyl cyclopentane-1,1-dicarboxylate

Product 1

HCID 18317887HCID 18317887, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cyclopentane-1,1-dicarboxylic acid dimethyl ester (4.0 g, 21.5 mmol) in MeOH (25 mL) is added potassium hydroxide (1.32 g, 23.7 mmol). The mixture is stirred at room temperature for 15 hours and concentrated under reduced pressure. To the obtained residue, aqueous 1M HCl (50 mL) is added and the solution is extracted with AcOEt. The organic layer is washed with H2O, dried over Na2SO4, and concentrated under reduced pressure to give cyclopentane-1,1-dicarboxylic acid methyl ester (3.72 g, quant.); TLC (dichloromrthane/MeOH, 10:1) Rf 0.25, 1H NMR (400 MHz, chloroform-d) δ ppm 1.67-1.74 (m, 4H), 2.17-2.25 (m, 4H), 3.75 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the obtained residue, aqueous 1M HCl (50 mL) is added
  3. extractionthe solution is extracted with AcOEt
  4. washThe organic layer is washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c7951baf90642d095ce6b3b7e269f9c
Source dataset
uspto-grants-2013_04
Patent number
US08420641B2

Reaction notes

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