4-{4-[2-(4-Propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester → 4-{4-[2-(4-Propyl-cyclohexyl)-ethyl]-phenyl}-cyclohexane carboxylic acid methyl ester

HRID 1893074Notes

Reaction equation

HRID 1893074 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>C1(C)C=CC=CC=1.C(O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH:19]3[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24]3)=[CH:15][CH:16]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 1

HCID 584532244-{4-[2-(4-Propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester

Product 1

HCID 584532124-{4-[2-(4-Propyl-cyclohexyl)-ethyl]-phenyl}-cyclohexane carboxylic acid methyl esterYield 80.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

6.41 g (17.4 mmol) of 4-{4-[2-(4-propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester produced in Example 5-1 was dissolved in a mixture of toluene and ethanol (1:1 by volume %). 0.4 g of Pd/C was added to 200 mL of the resultant solution and reacted in hydrogenation reactor for 12 hours. After reaction, Pd/C was removed by filtration and concentrated under reduced pressure to obtain 5.2 g (80%) of 4-{4-[2-(4-propyl-cyclohexyl)-ethyl]-phenyl}-cyclohexane carboxylic acid methyl ester.

Workup

  1. customreacted in hydrogenation reactor for 12 hours
  2. customwas removed by filtration
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c54f7fb0ab0424cb5945082aa63273c
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

Loading…