(E)-3-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]acrylic acid ethyl ester → 3-(4'-Propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester

HRID 386328Notes

Reaction equation

HRID 386328 reaction equation
[CH2:1]([O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)[CH3:2].[H][H]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:17][CH2:18]2)[CH2:9][CH2:8]1)[CH3:2]

Participants

5

Reactant 2

HCID 59289066(E)-3-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]acrylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 592890743-(4'-Propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(4′-Propyl-bicyclohexyl-4-yl)acrylic acid ethyl ester is hydrogenated in THF in the presence of palladium on charcoal. After 1 eq. of hydrogen has been consumed the catalyst is filtered off, the solvent is evaporated and the residue is filtered through silica yielding 3-(4′-propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester as a colourless oil.

Workup

  1. filtrationis filtered off
  2. customthe solvent is evaporated
  3. filtrationthe residue is filtered through silica

Sources & evidence

ORD record
ord-396de578a3024c949f759ad8625a62f9
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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