Damascenone → 2,6,6-Trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien-5-one

HRID 1076796Notes

Reaction equation

HRID 1076796 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[C:10](=[O:14])[CH:11]=[CH:12][CH3:13].[Se]=[O:16]>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5](=[O:16])[C:4]([CH3:8])([CH3:9])[C:3]=1[C:10](=[O:14])[CH:11]=[CH:12][CH3:13]

Participants

4

Reactant 2

HCID 62775DamascenoneHCID 167175Oxyselenide

Product 1

HCID 538173882,6,6-Trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien-5-oneYield 90.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.5 g (13 mMole) of 2,6,6-trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien [prepared according to the method given in Helv. Chim. Acta 54, 1899 (1971)] dissolved in 50 ml of dioxane were heated, under nitrogen atmosphere, during 45 min. at 60°, in the presence of 1.8 g (16 mMole) of selenium oxide. The reaction mixture was then cooled, concentrated under reduced pressure, and the obtained residue, diluted with 50 ml of acetic acid, was finally stirred at room temperature for 2 hours in the presence of 6 g of Raney nickel. The reaction mixture was then filtered, evaporated to dryness and the obtained residue was distilled (b.p. 100°-110°/o.2 Torr) to afford 2.4 g of a material containing 80 % of the desired keto compound.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated under reduced pressure
  3. additionthe obtained residue, diluted with 50 ml of acetic acid
  4. filtrationThe reaction mixture was then filtered
  5. customevaporated to dryness
  6. distillationthe obtained residue was distilled (b.p. 100°-110°/o.2 Torr)

Sources & evidence

ORD record
ord-0ff78fe7c109440195d6ffb28d8d05d7
Source dataset
uspto-grants-1976_05
Patent number
US03957877

Reaction notes

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