HCID 178418361, compound → HCID 178444480, compound

HRID 246789Notes

Reaction equation

HRID 246789 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>C(O)C.[Pd]>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178444479HCID 178444479, compound

Product 1

HCID 178444480HCID 178444480, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

41.6 g of ethyl β-(trans-4-pentylcyclohexyl)acrylate were dissolved in 368 ml of ethanol, treated with 7.4 g of palladium/carbon (5%) and hydrogenated at room temperature and under normal pressure until the hydrogen uptake came to a standstill (hydrogen uptake 0.167 mol). The mixture was gassed with nitrogen and filtered (rinsing with ethanol and methylene chloride). Concentration of the filtrate in vacuo gave 38.4 g of ethyl β-(trans-4-pentylcyclohexyl)propionate as a colourless oil which was distilled in a high vacuum; b.p. 113°-121° C./0.05-0.06 mmHg.

Workup

  1. filtrationfiltered
  2. wash(rinsing with ethanol and methylene chloride)

Sources & evidence

ORD record
ord-4431ae26d44e43faa9c2990129ec0f47
Source dataset
uspto-grants-1987_11
Patent number
US04704005

Reaction notes

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