N,N-Dimethylaniline → 4-(11-Acryloyloxyundecyl)phenol

HRID 1895816Notes

Reaction equation

HRID 1895816 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.CN(C)C1C=CC=CC=1>O1CCCC1.C(OCC)C>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 13140Acryloyl chlorideHCID 137127764-(11-Hydroxyundecyl)phenol

Product 1

HCID 593864904-(11-Acryloyloxyundecyl)phenolYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.5 ml of acryloylchloride was added to a solution of 7.4 g of 4-(11-hydroxyundecyl)-phenol (D) and 3.9 ml of N,N-dimethylaniline in 60 ml of tetrahydrofuran, cooled in an ice bath. After stirring for three hours at room temperature, the solution was diluted with 60 ml of diethyl ether and extracted subsequently with 100 ml of water, 100 ml of 2.4 N HCl and 100 ml of a saturated NaCl solution. 4.74 g of 4-(11-acryloyloxyundecyl)phenol (G, 53%) was obtained as a brown powder after drying over magnesium sulphate, evaporating and washing with ligroin.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted subsequently with 100 ml of water, 100 ml of 2.4 N HCl and 100 ml of a saturated NaCl solution

Sources & evidence

ORD record
ord-b93508280abd4093b2ce9d799f055171
Source dataset
uspto-grants-2013_08
Patent number
US08518299B2

Reaction notes

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