Iodoethane → HCID 4771099, compound

HRID 1771142Notes

Reaction equation

HRID 1771142 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[O:7].C([O-])([O-])=O.[K+].[K+].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH3:13][O:12][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH2:20][CH3:21])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 4771099HCID 4771099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 250 ml three necked flask, equipped with reflux condenser, mechanical stirrer, 18.2 g (100 mmol) of 3,5-dimethoxy-4-hydroxybenzaldehyde, 28 g (200 mmol) of dry K2CO3 and 100 ml of dry dimethylformamide are placed in argon condition. The mixture is stirred for 20 min in argon condition, then 42 g (21.7 ml, 270 mmol) of ethyliodide is added. The mixture is refluxed in argon condition with stirring for 20 h at 70÷100° C., and concentrated in vacuum at 50÷80° C. to dryness. Then 200 ml of water is added to the residue and the mixture is extracted with (4×100 ml) of methylene chloride. The combined organic fraction is washed with 7% NaOH solution, dried over magnesium sulfate, filtered off, concentrated in vacuum at 50÷80° C. The residue (20 g of oil) is used on the next step without further purification.

Workup

  1. temperaturewith reflux condenser, mechanical stirrer
  2. temperatureThe mixture is refluxed in argon condition
  3. stirringwith stirring for 20 h at 70÷100° C.
  4. concentrationconcentrated in vacuum at 50÷80° C. to dryness
  5. additionThen 200 ml of water is added to the residue
  6. extractionthe mixture is extracted with (4×100 ml) of methylene chloride
  7. washThe combined organic fraction is washed with 7% NaOH solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered off
  10. concentrationconcentrated in vacuum at 50÷80° C
  11. customThe residue (20 g of oil) is used on the next step without further purification

Sources & evidence

ORD record
ord-63981ffae0af4780b6afda2846b38ba9
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

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