Sodium Hydroxide → 3,3-Difluorocyclobutane-1,1-dicarboxylic acid

HRID 539975Notes

Reaction equation

HRID 539975 reaction equation
C([O:4][C:5]([C:7]1([C:13]([O:15]C(C)C)=[O:14])[CH2:10][C:9]([F:12])([F:11])[CH2:8]1)=[O:6])(C)C.[OH-].[Na+]>CO>[F:11][C:9]1([F:12])[CH2:10][C:7]([C:5]([OH:6])=[O:4])([C:13]([OH:15])=[O:14])[CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71255077HCID 71255077, compound

Product 1

HCID 534250953,3-Difluorocyclobutane-1,1-dicarboxylic acidYield 184.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,3-difluoro-cyclobutane-1,1-dicarboxylic acid diisopropyl ester (5.00 g, 18.9 mmol) and sodium hydroxide (3.00 g, 75.7 mmol) in methanol (20 ml) was stirred at room temperature overnight. The formed off-white solid was collected by filtration, washed with ethyl acetate, and dissolved in water. The aqueous solution was acidified with hydrochloric acid (3 N) to pH 3-4. The mixture was concentrated in vacuo to afford 6.293 g of the crude 3,3-difluorocyclobutane-1,1-dicarboxylic acid as a white solid, which was used for next step without further purification.

Workup

  1. filtrationThe formed off-white solid was collected by filtration
  2. washwashed with ethyl acetate
  3. dissolutiondissolved in water
  4. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-29345f0defc047c8bc785c3f1f95af49
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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