Iodoethane → HCID 4771099, compound

HRID 1769168Notes

Reaction equation

HRID 1769168 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH2:14][CH3:15])[CH:1]=[O:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 4771099HCID 4771099, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of syringaldehyde (50 g, 0.275 mol), ethyl iodide (85.8 g, 0.55 mol) and potassium carbonate (151.7 g, 1.09 mol) in DMF (60 ml) was stirred and heated at 60°-70° for 6 h. The mixture was cooled and evaporated in vacuo then treated with water and extracted with diethyl ether. The extracts were dried (Na2SO4) and evaporated to give the title compound (59 g) as a white solid, pure by tlc, and used without further purification.

Workup

  1. temperatureheated at 60°-70° for 6 h
  2. temperatureThe mixture was cooled
  3. customevaporated in vacuo
  4. additionthen treated with water
  5. extractionextracted with diethyl ether
  6. dry with materialThe extracts were dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-40e40ac93e2a42909365b75a9b9f197b
Source dataset
uspto-grants-1995_01
Patent number
US05380759

Reaction notes

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