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

HRID 373457

반응식

HRID 373457 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 72%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a 1 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser fitted with a nitrogen inlet tube, was added 20.0 g (39.77 mmol) (4-carbomethoxy) benzyltriphenylphosphonium bromide; 7.83 g (47.73 mmol) methyl 4-formylbenzoate; and 110 mL 2:1 methanol: toluene. After the starting material dissolved, 10.0 mL (43.75 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, washed with 2:1 methanol: toluene, and dried in a vacuum oven to afford 5.54 g (72%) of the compound as a 57:43 mixture of cis: trans isomers.

후처리

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

출처 및 근거

ORD 기록
ord-cdafc08746c54bb2b0d1586fd2da73e7
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164100

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