Sodium Iodide → HCID 86736282, compound

HRID 1390191Notes

Reaction equation

HRID 1390191 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([CH3:11])[CH:5]=[CH:6][CH2:7][CH:8]([CH3:10])[CH3:9].[I-:12].[Na+]>CC(CC(C)C)=O.CCOCC>[I:12][CH2:2][CH2:3][C@H:4]([CH3:11])/[CH:5]=[CH:6]\[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 5238Sodium Iodide2×HCID 54246504HCID 54246504, compound

Product 1

HCID 86736282HCID 86736282, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 4.4 g of (S)-1-chloro-3,7-dimethyl-4-octene in 30 ml of isobutyl methyl ketone is stirred at 130° for 37 hours with 7.55 g of sodium iodide. A further 3.75 g of sodium iodide are added thereto and the mixture is stirred further for 4 hours. After cooling to room temperature, the mixture is diluted with ether, washed with water, dried and concentrated under reduced pressure. The residue is pre-purified by adsorption on silicagel (elution agent: n-hexane), pure fractions are combined and distilled at 14 Torr and 130°. These are obtained 5.6 g (83.5%) of (S)-cis-1-iodo-3,7-dimethyl-4-octene as a colourless liquid. [α]D20 = +14.3° (2.21% in CHCl3).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is pre-purified by adsorption on silicagel (elution agent: n-hexane), pure fractions
  5. distillationdistilled at 14 Torr and 130°

Sources & evidence

ORD record
ord-d17e8fecbc60466fa27b1040a4d996bb
Source dataset
uspto-grants-1979_02
Patent number
US04138289

Reaction notes

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