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

HRID 2425808

Reaction equation

HRID 2425808 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 579729461,1'-[1,4-Phenylenedi(ethene-2,1-diyl)]bis[4-(pentadecyloxy)benzene]Yield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 dropwise at room temperature (25° C.). The resultant 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, and the resultant was stirred. The precipitate 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.

Workup

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

Sources & evidence

ORD record
ord-cdcd12e80e8442a18c2750ed3fe61c68
Source dataset
uspto-grants-2011_06
Patent number
US07965534B2

Linked notes

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