Iodoethane → HCID 4771099, compound

HRID 1491956Notes

Reaction equation

HRID 1491956 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-d438b9bd90ec4ef99743373d0595beb1
Source dataset
uspto-grants-1994_12
Patent number
US05371219

Reaction notes

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