Hydrochloric Acid → 4,4-Difluorocyclohex-1-ene-1-carboxylic acid

HRID 1160623Notes

Reaction equation

HRID 1160623 reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][C:5]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[CH:4][CH2:3]1.[OH-].[Na+].Cl>CO.C1COCC1>[F:1][C:2]1([F:18])[CH2:7][CH2:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68717850Benzyl 4,4-difluorocyclohex-1-ene-1-carboxylate

Product 1

HCID 687178884,4-Difluorocyclohex-1-ene-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above ester (0.58 g, 2.29 mmol) in 6 mL of methanol and 0.5 mL of THF was added 2.5 mL of 1 molar sodium hydroxide solution. The solution was stirred for 4 hours at ambient temperature, and then the pH was adjusted to 6 by the addition of 2 M HCl. The reaction mixture was men concentrated under vacuum, and the residue was azeotroped with toluene to provide 4,4-difluorocyclohex-1-ene-1-carboxylic acid an oily solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-df13731520b843dfb197dbdf37d68ee2
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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