Water → 4-Amino-2,6-dimethylbenzaldehyde

HRID 1360772Notes

Reaction equation

HRID 1360772 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 1 N 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-e2c5d39791c94690a987098974cebd1b
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

Loading…