4,8-Cyclododecadien-1-one → Cyclododecanone

HRID 270749Notes

Reaction equation

HRID 270749 reaction equation
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[H][H]>[Pd]>[C:1]1(=[O: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

4

Reactant 2

HCID 6011764,8-Cyclododecadien-1-oneHCID 178418361HCID 178418361, compound3×

Product 1

HCID 13246Cyclododecanone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

50 g of cyclododeca-4,8-dienone (isomer mixture, fraction 2 from Example 4) and 1 g of Pd/C catalyst (10% by weight of Pd, commercially available from Degussa under the product number E 101 N/D) were introduced into a 100 ml autoclave. 5 bar of hydrogen were injected with stirring. At a reaction temperature of 50° C., further hydrogen was supplied (10 h) until no more hydrogen was absorbed. After cooling, decompressing and filtering off the catalyst, the effluent was analyzed by gas chromatography. The conversion of cyclododeca-4,8-dienone was quantitative. Cyclododecanone was obtained in a substantially quantitative yield (>98%). The only impurities which could be detected by GC-MS were traces of cyclododecane, cyclododecenone and dodecanal.

Workup

  1. custom(10 h)
  2. customwas absorbed
  3. temperatureAfter cooling
  4. filtrationfiltering off the catalyst

Sources & evidence

ORD record
ord-058b4f14f2a646f8a5fa571c6fbabc07
Source dataset
uspto-grants-2008_11
Patent number
US07449606B2

Reaction notes

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