8-Hydroxyquinoline → 7-Dodecenyl-8-hydroxyquinoline

HRID 2072378

반응식

HRID 2072378 반응식
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH-].[Na+].[I-].[K+].[CH:16](Cl)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CO>[CH:16]([C:3]1[C:2]([OH:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

6

반응물 4

HCID 19238-HydroxyquinolineHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 1229391-Chlorododec-1-ene

생성물 1

HCID 537619667-Dodecenyl-8-hydroxyquinoline

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
230 °C

실험 절차

One hundred forty five grams (1.0 mole) 8-hydroxyquinoline, 40 gm. sodium hydroxide, 500 ml. methanol and 5 gm. potassium iodide were combined in a two liter round bottom flask. To this was added 243 gm. dodecenyl chloride (as used in Example I) and the mixture stirred under reflux overnight. The product was filtered, taken up in ether and washed with 500 ml. Claisen's alkali (in five portions). The ether solution was washed several times with water until neutral, dried and the solvent stripped to yield 317.9 gm. of crude product. Of this amount, 310.9 gm. was distilled through a one foot Vigreaux after being heated in the pot to 230° C. and cooled to about 100° C. The fractions coming off at 197°-202° C., 0.7 mm. Hg. (51.1 gm.) and 202°-231° C., 0.8 mm. Hg. (96.8 gm.) consisted almost entirely of 7-dodecenyl-8-hydroxyquinoline.

후처리

  1. additionTo this was added 243 gm
  2. temperatureunder reflux overnight
  3. filtrationThe product was filtered
  4. washwashed with 500 ml
  5. washThe ether solution was washed several times with water until neutral,
  6. customdried
  7. customto yield 317.9 gm
  8. distillationwas distilled through a one foot Vigreaux
  9. temperaturecooled to about 100° C
  10. customcoming off at 197°-202° C.
  11. custom(51.1 gm.) and 202°-231° C., 0.8 mm. Hg

출처 및 근거

ORD 기록
ord-70579c5f51074fc695ba85946918b221
출처 데이터셋
uspto-grants-1977_09
특허 번호
US04051223

연결된 노트

불러오는 중…