Iodine → 6,10-Dimethyl-1,5,9-undecatriene

HRID 1729757Notes

Reaction equation

HRID 1729757 reaction equation
[Mg].II.[CH2:4](Cl)/[CH:5]=[C:6](/[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])\[CH3:7].[CH2:15](Cl)[CH:16]=[CH2:17].[NH4+].[Cl-]>CCOCC>[CH3:7][C:6]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:5][CH2:4][CH2:17][CH:16]=[CH2:15]

Participants

7

Reactant 5

HCID 807IodineHCID 7850Allyl chlorideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 6372219Geranyl chloride

Product 1

HCID 911506,10-Dimethyl-1,5,9-undecatriene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Degreased magnesium turnings (84 g., 3.5 mole) were suspended in absolute ether (100 ml.). The Mg was activated with one crystal of iodine. In the course of about 3 hours, 300 g. (1.75 mole) of geranyl chloride, then 268 g. (3.5 mole) of allyl chloride in 800 ml. of ether were added dropwise. The mixture was boiled for 4 hours, then it was cooled and poured into a solution of 200 g. of NH4Cl in 1 liter of ice water. The solution was extracted with ether. The extracts were treated as usual, after concentration, they gave 384 g. of crude 6,10-dimethyl-1,5,9-undecatriene which was used without further purification.

Workup

  1. customIn the course of about 3 hours, 300 g
  2. temperatureit was cooled
  3. additionpoured into a solution of 200 g
  4. extractionThe solution was extracted with ether
  5. additionThe extracts were treated as usual,
  6. concentrationafter concentration, they
  7. customgave 384 g
  8. customof crude 6,10-dimethyl-1,5,9-undecatriene which was used without further purification

Sources & evidence

ORD record
ord-df7281c0d15548fa932989c13cc4ad72
Source dataset
uspto-grants-1976_11
Patent number
US03989739

Reaction notes

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