Iodine → HCID 20306124, compound

HRID 2419332Notes

Reaction equation

HRID 2419332 reaction equation
[Mg].Cl[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].II.[CH:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18]>CCOCC>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[CH2:3][CH:14]([OH:19])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 807Iodine2×HCID 72122,4-Dichlorobenzyl chloride2×HCID 8063PentanalHCID 5462224Magnesium

Product 1

HCID 20306124HCID 20306124, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 7.5g (0.384 mole) of magnesium turnings in 150 ml of ether is added a 10.0g (0.051 mole) portion of α,2,4-trichlorotoluene and a few crystals of iodine. When the iodine color has dissipated, the reaction is warmed to reflux, and 58.0g (0.297 mole) of additional α,2,4-trichlorotoluene in 50 ml of ether is added at such a rate that the refluxing is maintained. When the addition is complete, the reaction is stirred at reflux for 2 hours and cooled. To this reaction mixture is added 17.0g (0.197 mole) of valeraldehyde, and the reaction is heated again at reflux for 2 hours. The reaction is cooled and poured into ice cold dilute hydrochloric acid, and the organic phase is separated. The aqueous solution is extracted with ether, and the extract is combined with the organic phase. After a water wash, the organic solution is dried over anhydrous magnesium sulfate and stripped of solvent to give 57.2g of crude product. A distillation provides 11.3g (23%) of the product. Purity is determined by glc.

Workup

  1. temperaturethe reaction is warmed
  2. temperatureto reflux
  3. temperatureis maintained
  4. additionWhen the addition
  5. temperatureat reflux for 2 hours
  6. temperaturecooled
  7. temperaturethe reaction is heated again
  8. temperatureat reflux for 2 hours
  9. temperatureThe reaction is cooled
  10. additionpoured into ice cold dilute hydrochloric acid
  11. customthe organic phase is separated
  12. extractionThe aqueous solution is extracted with ether
  13. washAfter a water wash
  14. dry with materialthe organic solution is dried over anhydrous magnesium sulfate
  15. customto give 57.2g of crude product
  16. distillationA distillation

Sources & evidence

ORD record
ord-001e3a620789419fbab93195c3415c45
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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