Iodoethane → HCID 15453734, compound

HRID 1700269Notes

Reaction equation

HRID 1700269 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[CH3:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=1[OH:19]>C(#N)C.C(OCC)(=O)C>[CH2:7]([O:19][C:12]1[C:11]([CH3:10])=[C:16]([CH3:17])[CH:15]=[CH:14][C:13]=1[CH3:18])[CH3:8]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 170162,3,6-Trimethylphenol

Product 1

HCID 15453734HCID 15453734, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

734 mmol (101.5 g) of potassium carbonate and 917 mmol (143.1 g) of ethyl iodide are added in succession to a solution of 367 mmol (50 g) of 2,3,6-trimethylphenol in 1500 ml of acetonitrile. The whole is heated at reflux for 48 hours. The reaction mixture is subsequently cooled and then filtered and the filtrate is concentrated. The residue obtained is dissolved in ethyl acetate and washed with water and then with 10% aqueous sodium chloride solution. After drying the organic phase and then concentrating, an oily residue is obtained which is purified by chromatography on silica gel, using a petroleum ether: ethyl acetate mixture 95:5 as eluant, to yield the expected product.

Workup

  1. temperatureThe whole is heated
  2. temperatureat reflux for 48 hours
  3. temperatureThe reaction mixture is subsequently cooled
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. customThe residue obtained
  7. washwashed with water
  8. customAfter drying the organic phase
  9. concentrationconcentrating
  10. customan oily residue is obtained which
  11. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5fb49a9f523c47f28b006ce9c2445178
Source dataset
uspto-grants-2002_02
Patent number
US06350759B1

Reaction notes

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