Isopropanol → Fenofibrate

HRID 649355Notes

Reaction equation

HRID 649355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26].[CH:30](O)([CH3:32])[CH3:31]>>[CH3:31][CH:30]([O:27][C:25]([C:24]([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:9])=[CH:15][CH:14]=1)([CH3:29])[CH3:28])=[O:26])[CH3:32]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 749242-Bromo-2-methylpropanoic acidHCID 1235044-Hydroxy-4'-chlorobenzophenone

Product 1

HCID 3339FenofibrateYield 38.8%

Procedure

1 liter of isopropyl alcohol, 232.5 g (1 mol) of (4-chlorophenyl)(4-hydroxyphenyl)methanone, 138 g (1 mol) of potassium carbonate and 355 g (1.7 mol) of the 1-methylethyl ester of 2-bromo-2-methylpropanoic acid are introduced into a 4 liter reactor equipped with a stirrer and a condenser. The reaction medium is heated gently, with vigorous stirring, and then kept under reflux for 8 hours. About 400 ml of isopropyl alcohol are then distilled off, after which the medium is cooled, with stirring. The precipitate formed is filtered off and then washed with water in the heterogeneous phase, with shaking. It is filtered off and then washed again with 2% sodium hydroxide solution and then with water until the washings are neutral. The product is filtered off and purified by recrystallization from isopropyl alcohol to give 140 g of fenofibrate (yield=38.8%).

Workup

  1. customequipped with a stirrer and a condenser
  2. temperatureThe reaction medium is heated gently, with vigorous stirring
  3. temperatureunder reflux for 8 hours
  4. distillationAbout 400 ml of isopropyl alcohol are then distilled off
  5. temperatureafter which the medium is cooled
  6. customThe precipitate formed
  7. filtrationis filtered off
  8. washwashed with water in the heterogeneous phase
  9. stirringwith shaking
  10. filtrationIt is filtered off
  11. washwashed again with 2% sodium hydroxide solution
  12. filtrationThe product is filtered off
  13. custompurified by recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-2408557446a944e7861396d0e0284631
Source dataset
uspto-grants-1988_04
Patent number
US04739101

Reaction notes

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