Water → HCID 86651271, compound

HRID 1514974Notes

Reaction equation

HRID 1514974 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:6]([C:5]1[C:4]([CH3:11])=[CH:3][C:2]([O:1][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:9][C:8]=1[CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 86651271HCID 86651271, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-2,6-dimethylbenzaldehyde (100 mg) and 2-chloro-N,N-dimethylacetamide (89 mg) in DMF (2 mL) was added K2CO3 (185 mg) and the mixture was stirred at room temperature for 48 h. The mixture was poured into water and extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using 30% EtOAc/CH2Cl2 as eluent to give 2-(4-formyl-3,5-dimethylphenoxy)-N,N-dimethylacetamide as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2deea8613a1b4da1b812fea409638f71
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…