HCID 21249534, compound → 35720-57-1

HRID 1531603Notes

Reaction equation

HRID 1531603 reaction equation
[C:1]1(=[O:16])[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[H][H]>[Pd].C(O)C>[C:1]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21249534HCID 21249534, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2064037035720-57-1Yield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask was charged with cyclopentadeca-4E,12E-dien-1-one (0.10 g, 0.45 mmole), ethanol (5 ml) and 5% palladium-on-carbon (0.010 g). The mixture was stirred at room temperature under 1 atm of hydrogen gas for 30 minutes. The reaction mixture was filtered through celite and concentrated to provide crude cyclopentadec-4E-en-1-one (0.09 g, 88% yield). C15H30O (226.41 g/mole). 13CNMR (125 MHz, CDCl3): 21.65, 21.72, 25.85, 26.12, 27.86, 30.57, 31.02, 31.74, 31.82, 42.30, 42.49, 130.08, 132.00, 210.00 ppm. GC analysis indicates product to be a mixture of cyclopentadec-4E-en-1-one (39%), cyclopentadeca-4E,12E-dien-1-one (37%), and cyclopentadecanone (24%).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-40dabf65e31446a2990cfc655d93ad43
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

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