Water → 4-Amino-2,6-dimethylbenzaldehyde

HRID 1513268Notes

Reaction equation

HRID 1513268 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:15])[CH:7]=1)=O.O>CO.[OH-].[Na+]>[NH2:5][C:6]1[CH:7]=[C:8]([CH3:15])[C:9]([CH:13]=[O:14])=[C:10]([CH3:12])[CH:11]=1

Participants

5

Reactant 2

HCID 962WaterHCID 866328212,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)acetamide

Product 1

HCID 123812354-Amino-2,6-dimethylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of the above 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl) -acetamide in MeOH (30 mL) and 1N NaOH (30 mL) was stirred at RT overnight. To the suspension was added 100 mL of water and the solid was filtered, washed with water, and dried. The aqueous layer was extracted with EtOAc and the organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (heptane/EtOAc=4:1) to give the title compound. MS: m/z 150 (M+1).

Workup

  1. filtrationthe solid was filtered
  2. washwashed with water
  3. customdried
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography (heptane/EtOAc=4:1)

Sources & evidence

ORD record
ord-39becd3cb3aa4e51a964e6359bf1a513
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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