Hydrochloric Acid → p-Methylstyryl 1-anthraquinonyl ether

HRID 2291524

반응식

HRID 2291524 반응식
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl>CN1CCCC1=O>[C:2]1([O:1][CH:4]=[CH:5][C:6]2[CH:7]=[CH:8][C:13]([CH3:12])=[CH:14][CH:15]=2)[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 85121-HydroxyanthraquinoneHCID 24758Sodium hydride

생성물 1

HCID 86741659p-Methylstyryl 1-anthraquinonyl ether

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

0.1 mol of 1-hydroxyanthraquinone is dissolved hot in 100 ml of N-methylpyrrolidone in a 1 liter brown glass flask with a mechanical stirrer, thermometer and condenser. After the mixture has been cooled to room temperature, 0.1 mol of NaH suspension is added in portions. When the evolution of gas has ended, 0.11 mol of a mixture of 3- and 4-vinylbenzyl chloride is added and the mixture is stirred at 100° C. for 5 hours. Stirring is continued overnight at room temperature. 100 ml of 0.1N HCl are then added and the suspension thus formed is extracted several times by shaking with methylene chloride. After the extract has been neutralised with sodium bicarbonate solution and dried with Na2SO4 and the methylene chloride has been stripped off, an oil remains, from which a yellow crystalline product is precipitated with water. Crude yield: 33.7 g (99% of theory). The crude product is purified by column chromatography with methylene chloride; yield of m-/p-methylstyryl 1-anthraquinonyl ether=58% of theory, melting point: 88°-90° C.

후처리

  1. stirringStirring
  2. waitis continued overnight at room temperature
  3. customthe suspension thus formed
  4. extractionis extracted several times
  5. stirringby shaking with methylene chloride
  6. dry with materialdried with Na2SO4
  7. customis precipitated with water
  8. customThe crude product is purified by column chromatography with methylene chloride

출처 및 근거

ORD 기록
ord-70d1591bab204d569c597d01a72c5391
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04797347

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