1,4-Dioxane → 3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

HRID 1252791Notes

Reaction equation

HRID 1252791 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].C([N+]([O-:23])(CC)CC)C.O1CCOCC1>[Cu]Cl.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:23])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 123168Ethanamine, N,N-diethyl-, N-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 61.2%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

2.36 g (9.41 mmols) of 6-chloro-3,7-dimethyl-2,7-octadienyl acetate (purity: 92%), 92 mg (0.93 mmols) of copper(I) chloride and 3.65 g (29.6 mmols) of triethylamine N-oxide (purity: 95%) were placed in a flask, to which 5 ml of dioxane was added, followed by agitation of the mixture at 50° C. for 10 hours. 40 ml of water was added to the reaction mixture, after which it was extracted twice each with 70 ml of diethyl ether. The resultant extract was successively washed with each 20 ml of 3% sulfuric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated ammonium chloride aqueous solution, and dried with magnesium sulfate. The solvent was distilled off from the solution and the resultant residue was purified by column chromatography using silica gel [eluent: ethyl acetate/hexane (ratio by volume)=1/9-1/3], thereby obtaining 1.21 g of 8-acetoxy-2,6-dimethyl-2,6-octadienal. Yield: 61%. The results of the instrumental analysis were found to be substantially coincident with those obtained in Example 9(b).

Workup

  1. additionwas added
  2. extractionafter which it was extracted twice each with 70 ml of diethyl ether
  3. extractionThe resultant extract
  4. washwas successively washed with each 20 ml of 3% sulfuric acid
  5. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated ammonium chloride aqueous solution, and dried with magnesium sulfate
  6. distillationThe solvent was distilled off from the solution
  7. customthe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-1cbb944994e641289bb85aadaf01a85b
Source dataset
uspto-grants-1988_05
Patent number
US04745229

Reaction notes

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