HCID 21249534, compound → Cyclopentadecanone

HRID 1531602Notes

Reaction equation

HRID 1531602 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][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21249534HCID 21249534, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10409CyclopentadecanoneYield 89.1%

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 (0.01 g). The mixture was stirred at room temperature under 1 atm of hydrogen gas for 1 hour. The reaction mixture was filtered through celite and concentrated to provide cyclopentadecanone (exaltone) (0.09 g, 88% yield). C15H28O (224.39 g/mole). 1HNMR (500 MHz, CDCl3): 1.25 (m, 20H), 1.60 (m, 4H), 2.35 (t, 4H) ppm. 13CNMR (125 MHz, CDCl3): 23.40, 26.25, 26.39, 26.69, 26.74, 27.54, 42.05, 212.50, ppm. IR (νmax(cm−1)): 2924(s), 2854(s), 1708(s), 1458(m).

Workup

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

Sources & evidence

ORD record
ord-b5b4865663684e4abd7390d16a1690e9
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

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