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

HRID 1863831Notes

Reaction equation

HRID 1863831 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

A 30-ml four-necked flask was used, 7.87 g (23.7 mM) of p-pentadecanoxybenzaldehyde synthesized as described 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-percent by weight methylate was dropped thereto at room temperature (25° C.). Thereafter, aging was performed at a reflux temperature of 65° C. for 3 hours. Methanol was distilled out, and 200 ml of water was added to the residue, followed by agitation. Subsequently, the precipitate was filtrated. The resulting precipitate was further washed with water and acetone, followed by drying, so as to produce 7.49 g of 1,4-bis(4′-pentadecanoxystyryl)benzene isomer mixture (Compound (7)).

Workup

  1. customA 30-ml four-necked flask was used
  2. addition6.87 g (35.6 mM) of 28-percent by weight methylate was dropped
  3. customat room temperature
  4. custom(25° C.)
  5. distillationMethanol was distilled out
  6. addition200 ml of water was added to the residue
  7. filtrationSubsequently, the precipitate was filtrated
  8. washThe resulting precipitate was further washed with water and acetone
  9. customby drying

Sources & evidence

ORD record
ord-28e86a10ab5f40e7a68ea9e22227d7fa
Source dataset
uspto-grants-2009_12
Patent number
US07625499B2

Reaction notes

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