Sodium Iodide → 3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

HRID 1252790Notes

Reaction equation

HRID 1252790 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10](Cl)[C:11]([CH3:13])=[CH2:12])(=[O:3])[CH3:2].[I-].[Na+].C[N+]1([O-])CC[O:22]CC1.CN(C)C=O>O>[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH:12]=[O:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 82029Methyl morpholine oxideHCID 584614(6-Chloro-3,7-dimethylocta-2,7-dienyl) acetate

Product 1

HCID 566095533,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1.15 g (3.99 mmols) of 6-chloro-3,7-dimethyl-2,7-octadienyl acetate (purity: 80%), 0.91 g (6 mmols) of sodium iodide and 1.36 g (10 mmols) of N-methylmorpholine N-oxide (monohydrate) were placed in a flask, to which was added 5 ml of N,N-dimethylformamide. The mixture was agitated at 50° C. for 4 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction twice each with 70 ml of diethyl ether. The resulting extract was washed with each 20 ml of 3% sulfuric acid, a saturated sodium hydrogen carbonate aqueous solution and a 10% sodium sulfite aqueous solution, and dried with magnesium sulfate. After drying, the solvent was removed by distillation from the solution and the resulting residue was purified by column chromatography using silica gel [eluent: ethyl acetate/hexane (volume by ratio)=1/9-1/3], thereby obtaining 0.627 g of 8-acetoxy-2,6-dimethyl-2,6-octadienal. Yield: 75%. The results of an instrumental analysis of the 8-acetoxy-2,6-dimethyl-2,6-octadienal are as follows.

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction twice each with 70 ml of diethyl ether
  3. extractionThe resulting extract
  4. washwas washed with each 20 ml of 3% sulfuric acid
  5. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a 10% sodium sulfite aqueous solution, and dried with magnesium sulfate
  6. customAfter drying
  7. customthe solvent was removed by distillation from the solution
  8. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-4c61798d88054b23b98c5df4fc53e144
Source dataset
uspto-grants-1988_05
Patent number
US04745229

Reaction notes

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