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

HRID 1729759Notes

Reaction equation

HRID 1729759 reaction equation
[Mg].II.[CH2:4](Cl)[CH:5]=[CH2:6].[CH2:8](Cl)/[CH:9]=[C:10](/[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])\[CH3:11]>C(O)(=O)C.CCOCC>[CH3:11][C:10]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:9][CH2:8][CH2:6][CH:5]=[CH2:4]

Participants

7

Reactant 4

HCID 807IodineHCID 7850Allyl chlorideHCID 5462224MagnesiumHCID 6372219Geranyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium turnings (51 g., 2.1 mole) were suspended in 1700 ml. of ether and activated with a crystal of iodine. Allyl chloride (153 g., 2.0 mole) in 200 ml. of ether was added dropwise so as to maintain the mixture at reflux temperature throughout the addition. The mixture was refluxed for an additional 2 hours, then a solution of technical 82% pure geranyl chloride (210 g., 1.05 mole) in 200 ml. of ether was added dropwise at reflux temperature. The mixture was stirred for 2 hours at room temperature, then it was cooled down to 10° and slightly acidified with 20% aqueous acetic acid. The mixture was extracted with ether. The extracts were neutralised with 10% NaOH, washed with water, dried as usual and concentrated. The residue gave 217 g. of crude triene as a light yellow liquid the purity of which was 80% according to vapour phase chromatography; it was used without further purification.

Workup

  1. temperatureto maintain the mixture
  2. temperatureat reflux temperature
  3. additionthroughout the addition
  4. temperatureThe mixture was refluxed for an additional 2 hours
  5. temperatureat reflux temperature
  6. temperatureit was cooled down to 10°
  7. extractionThe mixture was extracted with ether
  8. washwashed with water
  9. customdried as usual and
  10. concentrationconcentrated
  11. customThe residue gave 217 g
  12. customit was used without further purification

Sources & evidence

ORD record
ord-b6aea2f141354ce3a63ac5342547e6a1
Source dataset
uspto-grants-1976_11
Patent number
US03989739

Reaction notes

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