Hydrochloric Acid → 4-Fluoro-1-hydroxycyclohex-3-ene-1-carboxylic acid

HRID 1160620Notes

Reaction equation

HRID 1160620 reaction equation
[F:1][C:2]1[CH2:7][CH2:6][C:5]([OH:18])([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:4][CH:3]=1.O.[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH2:7][CH2:6][C:5]([OH:18])([C:8]([OH:10])=[O:9])[CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68716576Benzyl 4-fluoro-1-hydroxycyclohex-3-ene-1-carboxylate

Product 1

HCID 687169194-Fluoro-1-hydroxycyclohex-3-ene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-fluoro-1-hydroxycyclohex-3-ene-1-carboxylate (0.554 g, 2.21 mmol) was dissolved in 27.5 mL of a 4:1 solution of THF:deionized water. A solution of 1 N NaOH was added to the reaction mixture. After stirring for 1.5 hours, the reaction mixture was acidified with 6 N HCl and extracted with EtOAc three times. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated to give 4-fluoro-1-hydroxycyclohex-3-ene-1-carboxylic acid as an oil.

Workup

  1. extractionextracted with EtOAc three times
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-744791e1045c4b5fa8367fbcc180e9ba
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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