P-Xylene → 4,4'-Bis(2,5-dimethylbenzyl)-1,1'-biphenyl

HRID 2035284

反応式

HRID 2035284 の反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1>[Ti](Cl)(Cl)(Cl)Cl.C(O)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:4]3[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=3[CH3:2])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 7809P-XyleneHCID 742754,4'-Bis(chloromethyl)-1,1'-biphenyl

生成物 1

HCID 585267414,4'-Bis(2,5-dimethylbenzyl)-1,1'-biphenyl

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 702Ethanol溶媒

実験手順

A 100mL flask was charged with 4,4′-bis(chloromethyl)-1,1′-biphenyl (1.0 g) and p-xylene (25 mL). To the clear solution stirring at room temperature was added titanium tetrachloride (6 drops) and the mixture instantly became dark brown. After stirring overnight at room temperature, ethanol (2mL) was added to kill the catalyst, and the mixture became a light, cream colored suspension. The mixture was transferred to a separatory funnel and washed with dilute aqueous HCl followed by saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, and concentrated to dryness under vacuum on a rotary evaporator. The tan solid was recrystallized from toluene yielding a white crystalline product, mp=144.6 C. GC/MS, HNMR, CNMR and IR were all consistent with the desired product.

後処理

  1. stirringAfter stirring overnight at room temperature
  2. customThe mixture was transferred to a separatory funnel
  3. washwashed with dilute aqueous HCl
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated to dryness under vacuum on a rotary evaporator
  6. customThe tan solid was recrystallized from toluene yielding a white crystalline product, mp=144.6 C

出典と根拠

ORDレコード
ord-b6cc3255943c4ee2ab27ee67d0f892cc
出典データセット
uspto-grants-2013_11
特許番号
US08574323B2

関連ノート

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