Potassium Hydroxide → HCID 18317887, compound

HRID 217241Notes

Reaction equation

HRID 217241 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 (dichloromethane/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-3e284a0d645a4a53a6c42f4f7e887f0b
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

Loading…