Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid

HRID 2232803노트

반응식

HRID 2232803 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:9][CH:10]=O)=[CH:4][CH:3]=1.[C:19]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21]C)=[O:20]>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:9]/[CH:10]=[CH:23]/[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 127223653,3-Bis(4-methylphenyl)-2-propenal

생성물 1

HCID 14347262(E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid수율 67.4%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

In the manner described in Example 99, 3,3-bis(4-methylphenyl) -2-propenal (9.45 g) was reacted with (carbomethoxymethylene)triphenylphosphorane (15.3 g) in carbon tetrachloride (95 ml) for 3 days at room temperature. The solvent was removed under reduced pressure and the residue was stirred at reflux in mixture of methanol (40 mL) and 2N NaOH for 45 minutes. The cooled solution was diluted with water (300 ml), extracted with dichloromethane (3×100 mL) to remove non-acidic material, and then acidified with 6N HCI (50 ML) and extracted with dichloromethane. The dried (MgSO4) extracts were evaporated and the crude product was crystallized from 2-propanol to afford 7.5 g of (E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid, mp 224.5°-226.5° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. temperatureat reflux in mixture of methanol (40 mL) and 2N NaOH for 45 minutes
  3. additionThe cooled solution was diluted with water (300 ml)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. customto remove non-acidic material
  6. extractionextracted with dichloromethane
  7. dry with materialThe dried (MgSO4) extracts
  8. customwere evaporated
  9. customthe crude product was crystallized from 2-propanol

출처 및 근거

ORD 기록
ord-c30e8d742eb6413787701c867cbd4a74
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788206

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