Water → 4-Amino-2,6-dimethylbenzaldehyde

HRID 1515008Notes

Reaction equation

HRID 1515008 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.[OH-].[Na+].O>CO>[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 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 866328212,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)acetamide

Product 1

HCID 123812354-Amino-2,6-dimethylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of the above 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)-acetamide was taken up in MeOH (30 mL) and 1N NaOH (30 mL) was stirred at ambient temperature overnight. Water (200 mL) was added and the resulting solid was filtered, washed with water, and dried to give 4-amino-2,6-dimethylbenzaldehyde. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (4:1) as eluent to give additional product.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-bdb7c40ad7e74a15be6e168d61108302
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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