4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid → HCID 69490583, compound

HRID 855467Notes

Reaction equation

HRID 855467 reaction equation
[OH:1][C@H:2]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:3][O:4][C:5](=[O:35])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1.[C:42]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][O:53][C:54]1[CH:62]=[CH:61][C:57]([C:58](O)=[O:59])=[CH:56][CH:55]=1)(=[O:45])[CH:43]=[CH2:44]>ClCCl>[C:42]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][O:53][C:54]1[CH:62]=[CH:61][C:57]([C:58]([O:1][C@H:2]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:3][O:4][C:5](=[O:35])[CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:34])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[O:59])=[CH:56][CH:55]=1)(=[O:45])[CH:43]=[CH2:44]

Participants

4

Reactant 2

HCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 69492200HCID 69492200, compound

Product 1

HCID 69490583HCID 69490583, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.56 g (2.7 mmole) of N,N-dicyclohexyl carbodiimide were added to a solution of 1.5 g (2.7 mmole) of (R)-4-(4-(6-acryloyloxyhexyloxy)benzoyloxy)cinnamic acid 2-hydroxy-2-phenyl-ethyl ester (21), 0.8 g (2.7 mmole) of 4-(6-acryloyloxy-hexyloxy)-benzoic acid (5) and 0.03 g (0.27 mmole) of 4-N,N-dimethylaminopyridine in 20 ml of dichloromethane, and cooled in an ice-water bath. After 3 h the ice-water bath was removed. The mixture was stirred at room temperature for two days. Then the mixture was filtered through a silica pad and the solvent was evaporated. After crystallization from ethanol, 1.2 g of the product (53%) were obtained with mp 97° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customAfter 3 h the ice-water bath was removed
  3. filtrationThen the mixture was filtered through a silica pad
  4. customthe solvent was evaporated
  5. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-76cd8bc327364235adf5a868ff5145e4
Source dataset
uspto-grants-2007_08
Patent number
US07261836B2

Reaction notes

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