4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid → HCID 69492436, compound

HRID 855468Notes

Reaction equation

HRID 855468 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6](=[O:16])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:2].[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)(=[O:20])[CH:18]=[CH2:19]>ClCCl>[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:15][C:12]2[CH:11]=[CH:10][C:9]([CH:8]=[CH:7][C:6]([O:5][CH2:4][O:3][CH2:1][CH3:2])=[O:16])=[CH:14][CH:13]=2)=[O:34])=[CH:31][CH:30]=1)(=[O:20])[CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 69491060HCID 69491060, compound

Product 1

HCID 69492436HCID 69492436, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.7 g (0.076 mole) of N,N-dicyclohexyl carbodiimide were added to a solution of 18.7 g (0.076 mole) of 4-hydroxycinnamic acid ethoxymethyl ester (23) (90% pure), 22.2 g (0.076 mole) of 4-(6-acryloyloxy-hexyloxy)-benzoic acid (5) and 0.93 g (0.0076 mole) of 4-N,N-dimethylaminopyridine in 200 ml of dichloromethane, cooled in an ice-water bath. After two hours the ice-water bath was removed. The mixture was stirred at room temperature overnight. Then it was filtered through a silica pad and the solvent was evaporated. 15 g of the product (40%) were obtained after crystallization from ethanol.

Workup

  1. temperaturecooled in an ice-water bath
  2. customAfter two hours the ice-water bath was removed
  3. filtrationThen it was filtered through a silica pad
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5d39299baebc41d1a701b792b2444e64
Source dataset
uspto-grants-2007_08
Patent number
US07261836B2

Reaction notes

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