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

HRID 5053

반응식

HRID 5053 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bdab6112829f4164810a4a13bdd2db90
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243021

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