(1,4-Phenylenebis(methylene))bis(triphenylphosphonium) dibromide → 1,1'-[1,4-Phenylenedi(ethene-2,1-diyl)]bis[4-(pentadecyloxy)benzene]

HRID 18945

Reaktionsgleichung

Reaktionsgleichung von HRID 18945
[CH2:1]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1C=CC([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:35][CH:34]=2)=CC=1.[Br-].[Br-]>CO>[CH2:1]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH:39][C:36]2[CH:35]=[CH:34][C:33]([CH:32]=[CH:21][C:20]3[CH:23]=[CH:24][C:17]([O:16][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:18][CH:19]=3)=[CH:38][CH:37]=2)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 2723797(1,4-Phenylenebis(methylene))bis(triphenylphosphonium) dibromideHCID 23127399p-Pentadecanoxybenzaldehyde

Produkt 1

HCID 579729461,1'-[1,4-Phenylenedi(ethene-2,1-diyl)]bis[4-(pentadecyloxy)benzene]Ausbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a 30 ml four-necked flask, 7.87 g (23.7 mM) of the p-pentadecanoxybenzaldehyde synthesized above and 8.65 g (11.0 mM) of p-xylylenebis(triphenylphosphonium bromide) were suspended in 100 ml of methanol, and 6.87 g (35.6 mM) of 28 wt % methylate was added thereto dropwise at room temperature (25° C.). The mixture was aged at a refluxing temperature of 65° C. for 3 hours. Methanol was removed by evaporation, and 200 ml of water was added to the residue, followed by stirring. The precipitate thus formed was collected by filtration, washed with water and acetone, and dried to give 7.49 g of a 1,4-bis(4′-pentadecanoxystyryl)benzene isomeric mixture (compound (1a)). The 1H-NMR data for identification were as follows.

Aufarbeitung

  1. addition6.87 g (35.6 mM) of 28 wt % methylate was added
  2. customdropwise at room temperature
  3. custom(25° C.)
  4. customMethanol was removed by evaporation, and 200 ml of water
  5. additionwas added to the residue
  6. customThe precipitate thus formed
  7. filtrationwas collected by filtration
  8. washwashed with water and acetone
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8f2b16e93d2844c8bda2fd82ce21cea6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07742112B2

Verknüpfte Notizen

Wird geladen…