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

HRID 1893077Notes

Reaction equation

HRID 1893077 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][CH2:27][CH2:28][CH3:29])[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][CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24]3)=[CH:15][CH:16]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 1

HCID 584532174-{4-[2-(4-Pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester

Product 1

HCID 584532084-{4-[2-(4-Pentyl-cyclohexyl)-ethyl]-phenyl}-cyclohexane carboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

6.9 g (17.4 mmol) of 4-{4-[2-(4-pentyl-cyclohexyl)-vinyl]-phenyl}cyclohexane carboxylic acid methyl ester produced in Example 6-1 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, concentrated under reduced pressure and recrystallized from chloroform and ethanol to obtain 6.1 g (88%) of 4-{4-[2-(4-pentyl-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
  4. customrecrystallized from chloroform and ethanol

Sources & evidence

ORD record
ord-0091151366e44444b24dc1fd0e3e3bcd
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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