Clofibrate → Clofibric Acid

HRID 1850001

Reaction equation

HRID 1850001 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.O.[OH-].[Li+]>O1CCCC1.O>[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 2

HCID 2796ClofibrateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 2797Clofibric AcidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-chloro-phenoxy)-2-methyl-propionic acid ethyl ester (2.0 g, 8.24 mmol) in tetrahydrofuran (16 mL) at room temperature is added water (4 mL) followed by lithium hydroxide monohydrate (0.69 g, 16.4 mmol). The reaction is stirred for 16 h at room temperature. After this time, the mixture is diluted with water and washed with DCM. The aqueous phase is separated, acidified to pH ˜2 with 1M aqueous HCl solution and then extracted with DCM (x2). The combined organic extracts are washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound as a white solid (1.45 g, 82%). 1H NMR (400 MHz, CHLOROFORM-d): δ ppm 1.62 (6H, s), 6.89 (2H, d, J=9.0 Hz), 7.24 (2H, d, J=9.0 Hz).

Workup

  1. washwashed with DCM
  2. customThe aqueous phase is separated
  3. extractionextracted with DCM (x2)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ebf3c5f299f465c8bf5d36d7c22816f
Source dataset
uspto-grants-2015_02
Patent number
US08957063B2

Linked notes

Loading…