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

HRID 1893071Notes

Reaction equation

HRID 1893071 reaction equation
CN(C)C(=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:15][O:16][C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18].[CH2:32]([CH:37]1[CH2:42][CH2:41][CH:40]([CH:43]=[CH2:44])[CH2:39][CH2:38]1)[CH2:33][CH2:34][CH2:35][CH3:36]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:15][O:16][C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:44]=[CH:43][CH:40]3[CH2:41][CH2:42][CH:37]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:38][CH2:39]3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18]

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 190391931-Pentyl-4-vinyl-cyclohexaneHCID 584532034-(4-Bromophenyl)cyclohexane carboxylic acid methyl ester

Product 1

HCID 584532174-{4-[2-(4-Pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl esterYield 62%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

180 mL of N,N-dimethylacetamide (DMA) solution including 12.8 g (60.1 mmol) of potassium phosphate, 14.3 g (48 mmol) of 4-(4-bromophenyl)cyclohexanecarboxylic acid methyl ester produced in Example 1-1, and 8.33 g (40 mmol) of 1-pentyl-4-vinyl-cyclohexane was poured to flask filled with Argon gas. Then, 0.17 g (catalytic amount) of palladium acetate was added to the flask and reacted in oil bath at 120° C. for 32 hours. After reaction, 100 mL of distilled water was added to the reaction mixture, extracted by ethyl acetate, and then the aqueous layer was extracted by chloroform. The organic layer was dried by Na2SO4, concentrated under reduced pressure, and then recrystallized from ethanol to obtain 9.8 g (62%) of 4-{4-[2-(4-pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester.

Workup

  1. additionwas poured to flask
  2. additionfilled with Argon gas
  3. customreacted in oil bath at 120° C. for 32 hours
  4. additionwas added to the reaction mixture
  5. extractionextracted by ethyl acetate
  6. extractionthe aqueous layer was extracted by chloroform
  7. dry with materialThe organic layer was dried by Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-14f5fc01f0c14d63b8ea886b39ed57ed
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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