(3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one → (R)-6,10-dimethyl-9-undecene-2-one

HRID 654589

Reaction equation

HRID 654589 reaction equation
[CH3:1][C@H:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH2:3]/[CH:4]=[CH:5]/[C:6](=[O:8])[CH3:7]>[Ni].C(OCC)(=O)C>[CH3:1][C@@H:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH3:14])[CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7]

Participants

4

Reactant 1

HCID 10965409(3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one

Product 1

HCID 11171582(R)-6,10-dimethyl-9-undecene-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 3 l, three-necked, round bottomed flask fitted with a mechanical stirrer was charged with 6 g of Raney-Nickel, 500 ml of ethyl acetate and 127 g of (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one. The flask was purged with hydrogen and stirring was initiated at room temperature. Hydrogenation was carried out under a pressure of 2 bar. After 2 hours the reaction was stopped. The total hydrogen uptake was about 14.2 l. The reaction mixture was filtered and concentrated to give a pale yellow oil of (R)-6,10-dimethyl-9-undecene-2-one which was distilled under vacuum using a 40 cm Vigreux distillation column, and the following fractions were collected:

Workup

  1. customA 3 l, three-necked, round bottomed flask fitted with a mechanical stirrer
  2. customThe flask was purged with hydrogen
  3. customwas initiated at room temperature
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-993cae18327140bf9d6091192b24e843
Source dataset
uspto-grants-1992_07
Patent number
US05132464

Linked notes

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