N,N-Dimethylaniline → HCID 59386502, compound

HRID 1895820Notes

Reaction equation

HRID 1895820 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][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1.CN(C)C1C=CC=CC=1.C(OCC)C>O1CCCC1>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 3283Diethyl EtherHCID 13140Acryloyl chlorideHCID 59386503HCID 59386503, compound

Product 1

HCID 59386502HCID 59386502, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.8 ml of acryloyl chloride was added to a solution of 2.2 g of 4-{2-[4-(6-Hydroxy-hexyloxy)-phenyl]-ethyl}-phenol (L) and 1.23 ml of N,N-dimethylaniline in 20 ml of tetrahydrofuran, cooled in an icebath. The mixture was stirred for 3 hours at room temperature. 40 ml of diethylether was added which was extracted twice with 20 ml of 2.4N hydrochloric acid and once with 20 ml of brine. It was dried over magnesium sulphate and evaporated. 1.65 g of 4-{2-[4-(6-acryloyloxy-hexyloxy)-phenyl]-ethyl}-phenol (N, 64%) was obtained after washing with 15 ml of pentane.

Workup

  1. temperaturecooled in an icebath
  2. extractionwas extracted twice with 20 ml of 2.4N hydrochloric acid and once with 20 ml of brine
  3. dry with materialIt was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-99546dd29c4a42b19350b06429d4ef0f
Source dataset
uspto-grants-2013_08
Patent number
US08518299B2

Reaction notes

Loading…