1-(3-Phenyl-1-propenyl)cyclododecane → 1-(3-Phenylpropyl)cyclododecane

HRID 129533Notes

Reaction equation

HRID 129533 reaction equation
[C:1]1([CH2:7][CH:8]=[CH:9][CH:10]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 544717161-(3-Phenyl-1-propenyl)cyclododecaneHCID 178418361HCID 178418361, compound

Product 1

HCID 152966211-(3-Phenylpropyl)cyclododecane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 6.4 g (22.5 mmoles) of 1-(3-phenyl-1-propenyl)cyclododecane in 50 mL of ethanol is added 0.48 g of 10% palladium on carbon. The reaction mixture is subjected to hydrogen (50 psi) atmosphere using a Paar hydrogenerator and shaken overnight after which time no starting material is evident by TLC. The reaction mixture is filtered through Celite which is washed with additional ethanol. The filtrate is evaporated and the crude residue (5.8 g) is used directly for the next step: NMR (CDCl3) δ 1.2-1.4 (m, 10H), 1.6 (m, 2H), 2.55 (t, 2H, J=8 Hz), 7.2 (m, 5H).

Workup

  1. filtrationThe reaction mixture is filtered through Celite which
  2. washis washed with additional ethanol
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-70ad60c7c9624cf6a26b5eb8f2075dbb
Source dataset
uspto-grants-1995_11
Patent number
US05468774

Reaction notes

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