Dicyclohexylcarbodiimide → Cyclohexane-1,4-dicarboxylic acid 1-[4-(11-acryloyloxy-undecyl)phenyl]ester 4-(4-hexylphenyl)ester

HRID 2357700Notes

Reaction equation

HRID 2357700 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)(=[O:19])[CH:17]=[CH2:18].[CH2:39]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1O)[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].[C@H:52]1([C:61](O)=[O:62])[CH2:57][CH2:56][C@H:55]([C:58]([OH:60])=[O:59])[CH2:54][CH2:53]1>ClCCl>[CH2:39]([C:45]1[CH:50]=[CH:49][C:48]([O:60][C:58]([CH:55]2[CH2:56][CH2:57][CH:52]([C:61]([O:38][C:35]3[CH:34]=[CH:33][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:16](=[O:19])[CH:17]=[CH2:18])=[CH:37][CH:36]=3)=[O:62])[CH2:53][CH2:54]2)=[O:59])=[CH:47][CH:46]=1)[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 185942-HexylphenolHCID 593864904-(11-Acryloyloxyundecyl)phenolHCID 178525731HCID 178525731, compound

Product 1

HCID 59386492Cyclohexane-1,4-dicarboxylic acid 1-[4-(11-acryloyloxy-undecyl)phenyl]ester 4-(4-hexylphenyl)esterYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g of N,N′-dicyclohexyl carbodiimide was added to a mixture of 2.0 g of 4-(11-acryloyloxyundecyl)phenol (G), 1.1 g of hexylphenol (E), 1.03 g of trans-cyclohexane-1,4-dicarboxylic acid (F), 0.15 g of 4-N,N-dimethylaminopyridine and 50 ml of dichloromethane, cooled in an ice bath and stirred under a nitrogen atmosphere. The mixture was stirred overnight at room temperature. 0.93 g of cyclohexane-1,4-dicarboxylic acid 1-[4-(11-acryloyloxy-undecyl)phenyl]ester 4-(4-hexylphenyl)ester (6, 25%) was obtained as a white powder after evaporation, and separation by chromatography using silica gel and dichloromethane/petroleum ether 97/3 as eluent.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe mixture was stirred overnight at room temperature

Sources & evidence

ORD record
ord-fd8d8dec088b4a7398f6eb374101182e
Source dataset
uspto-grants-2010_07
Patent number
US07763330B2

Reaction notes

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