4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid → HCID 58935103, compound

HRID 855464Notes

Reaction equation

HRID 855464 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[C:15]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1)(=[O:18])[CH:16]=[CH2:17]>ClCCl>[C:15]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([O:5][CH2:4][O:3][CH2:1][CH3:2])=[O:14])=[CH:8][CH:9]=2)=[O:32])=[CH:29][CH:28]=1)(=[O:18])[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 58935106HCID 58935106, compound

Product 1

HCID 58935103HCID 58935103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 42.2 g (0.20 mole) of 4-Hydroxy-benzoic acid ethoxymethyl ester (15) in 520 ml of dichloromethane were added 58.3 g (0.2 mole) of 4-(6-acryloyloxy-hexyloxy)-benzoic acid (5) and 2.4 g (0.02 mole) of 4-N,N-dimethylaminopyridine under N2 atmosphere. The mixture was cooled in an ice-water bath. After few minutes 41.15 g (0.2 mole) of N,N-dicyclohexyl carbodiimide were added. Then the ice-water bath was removed. It was stirred at room temperature under N2 for one night. Then the mixture was filtered and extracted twice with 300 ml of hydrochloric acid (2.4 M).

Workup

  1. temperatureThe mixture was cooled in an ice-water bath
  2. customThen the ice-water bath was removed
  3. filtrationThen the mixture was filtered
  4. extractionextracted twice with 300 ml of hydrochloric acid (2.4 M)

Sources & evidence

ORD record
ord-45de542d3d6e4cf3b0566402097c7fb6
Source dataset
uspto-grants-2007_08
Patent number
US07261836B2

Reaction notes

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