Vanillin → 2-[2-(4-Hydroxy-3-methoxyphenyl)-ethenyl]-quinoline

HRID 326173

반응식

HRID 326173 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH:20]=O)[CH:17]=[CH:16][C:15]=1[OH:22]>C(OC(=O)C)(=O)C>[OH:22][C:15]1[CH:16]=[CH:17][C:18]([CH:20]=[CH:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:19][C:14]=1[O:13][CH3:12]

참가 물질

4

반응물 2

HCID 1183VanillinHCID 70602-Methylquinoline

생성물 1

HCID 6239702-[2-(4-Hydroxy-3-methoxyphenyl)-ethenyl]-quinoline수율 63%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

In 61.34 g of acetic anhydride, 34.40 g of 2-methylquinoline and 36.57 g of vanilin were allowed to react with each other under reflux for 16 hours, and 50 cm3 of acetic acid was expelled by distillation. The residue and 250 cm3 of 3 N hydrochloric acid added thereto were heated for one hour. The heated mixture was cooled to deposit crystals, which were separated by filtration. The crystals were suspended in aqueous ammonia and stirred for one hour to expel hydrogen chloride from the crystals. The crystals thus freed from hydrogen chloride were again separated by filtration and collected. They were recrystallized via 2-ethoxyethanol to afford 2-[2-(4-hydroxy-3-methoxyphenyl)-ethenyl]-quinoline in a yield of 63%.

후처리

  1. customto react with each other
  2. temperatureunder reflux for 16 hours
  3. distillation50 cm3 of acetic acid was expelled by distillation
  4. additionThe residue and 250 cm3 of 3 N hydrochloric acid added
  5. temperaturethereto were heated for one hour
  6. temperatureThe heated mixture was cooled
  7. customwere separated by filtration
  8. customwere again separated by filtration
  9. customcollected
  10. customThey were recrystallized via 2-ethoxyethanol

출처 및 근거

ORD 기록
ord-387d3573d2a747e3b3a4c0d03dbf8937
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04444868

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