Hydrochloric Acid → Fenofibric Acid

HRID 733492Notes

Reaction equation

HRID 733492 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-:17].[Na+].C(Cl)(Cl)Cl.Cl>CC(C)=O.O>[CH3:4][C:5]([O:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][CH:15]=2)=[O:7])=[CH:13][CH:12]=1)([C:6]([OH:7])=[O:17])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 1235044-Hydroxy-4'-chlorobenzophenone

Product 1

HCID 64929Fenofibric AcidYield 145.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-4′-hydroxybezophenone (116 g, 0.500 mole) and sodium hydroxide (120 g, 3.00 mole) in acetone (1 L) was heated to reflux for 2 hours. The heating was stopped and the heating source was removed. A mixture of chloroform (179 g, 1.50 mole) in acetone (300 mL) was added drop-wise. The reaction mixture was stirred overnight without heating. The mixture was heated to reflux for 8 hours and then allowed to cool to room temperature. The precipitate was removed by filtration and washed with acetone (100 mL). The filtrate was concentrated under reduced pressure to give a brown oil. Water (200 mL) was added to the brown oil and was acidified (to pH=1) with 1N hydrochloric acid. The precipitate, which formed was filtered and dried under high vacuum. The remaining yellow solid (268 g) was recrystallized from toluene in 4 batches (400 mL toluene each). After filtration and drying under high vacuum, the experiment produced fenofibric acid (116 g, 73% yield) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customthe heating source was removed
  4. additionwas added drop-wise
  5. temperaturewithout heating
  6. temperatureThe mixture was heated
  7. temperatureto reflux for 8 hours
  8. customThe precipitate was removed by filtration
  9. washwashed with acetone (100 mL)
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customto give a brown oil
  12. customThe precipitate, which formed
  13. filtrationwas filtered
  14. customdried under high vacuum
  15. customThe remaining yellow solid (268 g) was recrystallized from toluene in 4 batches (400 mL toluene each)
  16. filtrationAfter filtration
  17. customdrying under high vacuum

Sources & evidence

ORD record
ord-e1171e8cd577444588b1158b8a3f6f65
Source dataset
uspto-grants-2009_09
Patent number
US07589233B2

Reaction notes

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