Hydrochloric Acid → Clofibric Acid

HRID 1919991Notes

Reaction equation

HRID 1919991 reaction equation
C([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[Li+].[OH-].Cl>C1COCC1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:16])=[O:3])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2796ClofibrateHCID 3939Lithium Hydroxide

Product 1

HCID 2797Clofibric Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-chlorophenoxy)isobutyric acid ethyl ester (1.0 g, 4.12 mmol) in THF (10 mL) was treated with 1N aqueous LiOH (10 mL) and stirred overnight at room temperature. The mixture was acidified with 1N aqueous HCl to pH 3-4 and extracted three times with EtOAc. The combined organic layers were dried and concentrated to give the title compound.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-806fde1552b4449a93aca0824f7fddce
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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