Potassium Carbonate → HCID 86623125, compound

HRID 536080Notes

Reaction equation

HRID 536080 reaction equation
I[CH2:2][CH2:3][CH3:4].[OH:5][C:6]1[C:7]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:18][O:17][CH2:16][CH2:15][O:14][C:7]1[C:6]([O:5][CH2:2][CH2:3][CH3:4])=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 86623124HCID 86623124, compound

Product 1

HCID 86623125HCID 86623125, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Iodopropane (3.09 mL, 31.60 mmol) was added to a solution of 3-hydroxy-2-(2-methoxyethoxy)benzaldehyde (3.1 g, 15.8 mmol) and potassium carbonate (4.37 g, 31.60 mmol) in DMF (80 mL) and the mixture was stirred at 100° C. overnight under a nitrogen atmosphere. The reaction mixture was partitioned between saturated ammonium chloride (aq.) and CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated to give the title compound in quantitative yield (3.8 g) as an oil. This material was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between saturated ammonium chloride (aq.) and CH2Cl2
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-edabde16cce449a79772a414d0469b98
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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