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

HRID 970245Notes

Reaction equation

HRID 970245 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, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 42.2 g (0.20 mole) of 4-hydroxy-benzoic acid ethoxymethyl ester (11) in 520 ml of dichloromethane were added 58.3 g (0.2 mole) of 4-(6-acryloyloxy-hexyloxy)-benzoic acid and 2.4 g (0.02 mole) of 4-N,N-dimethylaminopyridine, under a nitrogen atmosphere. The mixture was cooled in an ice-water bath. After a 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 nitrogen for one night. Then the mixture was filtered and extracted twice with 300 ml of hydrochloric acid (2.4 M). The organic layer was passed through a filter paper and the solvent was evaporated to leave 98.5 g of a clear oil (100%).

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)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a63710ad85b14765b44f2cde0fae0d32
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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