Sodium Hydroxide → 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352076Notes

Reaction equation

HRID 352076 reaction equation
C([O:4][CH2:5][C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][CH:10]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][CH2:5][C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 129928464-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

Product 1

HCID 129928474-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(Acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]-ethenyl]-1,3-oxazole (1556 g, 2.23 mol), 2N-aqueous sodium hydroxide solution (2.4 L, 4.8 mol) and activated carbon (47 g) were added to methanol (4.7 L), and the mixture was refluxed under stirring for 1 hour. The activated carbon and the insoluble material were removed by filtration under pressurization. The residue was washed with methanol/water (2:1) (470 ml). The washing solution was combined with the filtrate and the mixture was refluxed. Water (3.3 L) was added at the same temperature. After allowing to cool to room temperature and stirring, the mixture was stirred at the same temperature for 1 hour. The precipitated crystals were collected by filtration, washed with water (4.7 L) and dried under reduced pressure to give 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (568.5 g, 2.11 mol, yield 95%).

Workup

  1. temperaturethe mixture was refluxed
  2. customThe activated carbon and the insoluble material were removed by filtration under pressurization
  3. washThe residue was washed with methanol/water (2:1) (470 ml)
  4. temperaturethe mixture was refluxed
  5. additionWater (3.3 L) was added at the same temperature
  6. stirringstirring
  7. stirringthe mixture was stirred at the same temperature for 1 hour
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with water (4.7 L)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-833bbb79775740f6a3d286ca9602bef0
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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