N,N-Dimethylaniline → 11-Acryloyloxyundecyl phenol

HRID 2357699Notes

Reaction equation

HRID 2357699 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](O)=[CH:20][CH:19]=1.CN(C)C1C=CC=CC=1.[O:34]1CCCC1>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:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:34])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8028TetrahydrofuranHCID 13140Acryloyl chlorideHCID 137127764-(11-Hydroxyundecyl)phenol

Product 1

HCID 8676114811-Acryloyloxyundecyl phenolYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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-809d1bc572394be99c7d282be9b49f77
Source dataset
uspto-grants-2010_07
Patent number
US07763330B2

Reaction notes

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