Toluene → 4,4'-Bis(carbomethoxy)stilbene

HRID 5053

反応式

HRID 5053 の反応式
[Br-].[C:2]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)([O:4][CH3:5])=[O:3].[CH:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)=O.C1(C)C=CC=CC=1.C[O-].[Na+]>CO>[C:38]([C:37]1[CH:42]=[CH:43][C:34]([CH:32]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]([C:2]([O:4][CH3:5])=[O:3])=[CH:31][CH:30]=2)=[CH:35][CH:36]=1)([O:40][CH3:41])=[O:39]

参加物

6

反応物 4

HCID 1140TolueneHCID 15294Methyl 4-FormylbenzoateHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 10942334Sodium Methoxide

生成物 1

HCID 1391384,4'-Bis(carbomethoxy)stilbene収率 79.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 126.35 g (251 mmol) (4-carbomethoxy)benzyltriphenylphosphonium bromide, 49.45 g (302 mmol) methyl 4-formylbenzoate, and 632 mL 2:1 methanol:toluene. After the starting material dissolved, 63.2 mL (277 mmol) 25% sodium methoxide solution in methanol was added dropwise over several minutes. The reaction vessel was heated at reflux for 30 minutes. After cooling to room temperature, the reaction vessel was cooled at 0° C. for several hours. The resulting precipitate was filtered and dried in a vacuum oven to afford 59.0 g (79%) 4,4'-bis(carbomethoxy)stilbene as a 7:3 mixture of cis:trans isomers.

後処理

  1. customTo a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
  2. temperaturereflux condenser with a nitrogen inlet tube
  3. dissolutionAfter the starting material dissolved
  4. temperatureThe reaction vessel was heated
  5. temperatureat reflux for 30 minutes
  6. temperaturethe reaction vessel was cooled at 0° C. for several hours
  7. filtrationThe resulting precipitate was filtered
  8. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-bdab6112829f4164810a4a13bdd2db90
出典データセット
uspto-grants-1993_09
特許番号
US05243021

関連ノート

読み込み中…