Dicyclohexylcarbodiimide → 4-(6-Acryloyloxy-hexyloxy)-benzoic acid 4-{2-[4-(6-acryloyloxy-hexyloxy)-phenyl]-ethyl}-phenyl ester

HRID 1895821Notes

Reaction equation

HRID 1895821 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18].[C:43]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:54][C:55]1[CH:63]=[CH:62][C:58]([C:59](O)=[O:60])=[CH:57][CH:56]=1)(=[O:46])[CH:44]=[CH2:45]>ClCCl>[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][C:59](=[O:60])[C:58]3[CH:57]=[CH:56][C:55]([O:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][O:47][C:43](=[O:46])[CH:44]=[CH2:45])=[CH:63][CH:62]=3)=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 59386502HCID 59386502, compound

Product 1

HCID 593864984-(6-Acryloyloxy-hexyloxy)-benzoic acid 4-{2-[4-(6-acryloyloxy-hexyloxy)-phenyl]-ethyl}-phenyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.01 g of N,N′-dicyclohexyl carbodiimide was added to a mixture of 1.6 g of 4-{2-[4-(6-acryloyloxy-hexyloxy)-phenyl]-ethyl}-phenol (G), 1.43 g of 4-(6-acryloyloxyhexyloxy)benzoic acid, 0.06 g of 4-N,N-dimethylaminopyridine and 10 ml of dichloromethane stirred in an icebath. After stirring for 2 hours, the ice-bath was removed and the mixture was stirred one night at room temperature. 2.3 g of 4-(6-Acryloyloxy-hexyloxy)-benzoic acid 4-{2-[4-(6-acryloyloxy-hexyloxy)-phenyl]-ethyl}-phenyl ester (10, 78%) was obtained after filtration through silica, evaporation and recrystallizing from methanol.

Workup

  1. stirringAfter stirring for 2 hours
  2. customthe ice-bath was removed
  3. stirringthe mixture was stirred one night at room temperature

Sources & evidence

ORD record
ord-c963ca05648746fb93bca9d7a14858b5
Source dataset
uspto-grants-2013_08
Patent number
US08518299B2

Reaction notes

Loading…