Acetate → 2,6,6-Trimethyl-1-[2-pentenoyl]-2-cyclohexene

HRID 903299Notes

Reaction equation

HRID 903299 reaction equation
[C:1]([O-])(=O)C.[CH3:5][C:6]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:7][C:8](=[O:12])[CH:9]=[CH:10][CH3:11]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[CH3:5][C:6]1[CH:7]([C:8](=[O:12])[CH:9]=[CH:10][CH2:11][CH3:1])[C:16]([CH3:17])([CH3:18])[CH2:15][CH2:14][CH:13]=1

Participants

5

Reactant 2

HCID 175Acetate2×HCID 541583646,10-Dimethylundeca-2,5,9-trien-4-one

Product 1

HCID 571202852,6,6-Trimethyl-1-[2-pentenoyl]-2-cyclohexene

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolvent

Procedure

248 g. of the acetate prepared according to paragraph (c) were heated at 90° during 5 h. in the presence of 500 ml. of acetic acid and 10 g. of copper acetate. By means of vapour phase chromatography it was shown that the starting acetate had completely reacted. The mixture was concentrated in vacuum and the residue was treated with 300 ml. of water. After extraction with petrol-ether and the usual treatments, 190 g. of a mixture consisting of 7,11-dimethyl-5-oxo-3,6,10-dodecatriene and two isomeric ketones, 7,11-dimethyl-5-oxo-3,7,10-dodecatriene and 11-methyl-7-methylene-5-oxo-3,10-dedacadiene, were obtained.

Workup

  1. temperaturewere heated at 90° during 5 h. in the presence of 500 ml
  2. customhad completely reacted
  3. concentrationThe mixture was concentrated in vacuum
  4. additionthe residue was treated with 300 ml
  5. extractionAfter extraction with petrol-ether
  6. customwere obtained

Sources & evidence

ORD record
ord-76b9b35a0f1c4be8a4a37fffea7ae0fd
Source dataset
uspto-grants-1980_10
Patent number
US04226892

Reaction notes

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