Hydrochloric Acid → p-Methylstyryl 1-anthraquinonyl ether

HRID 653470

反応式

HRID 653470 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 85121-HydroxyanthraquinoneHCID 24758Sodium hydride

生成物 1

HCID 86741659p-Methylstyryl 1-anthraquinonyl ether

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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 0.1 N 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.

後処理

  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

出典と根拠

ORDレコード
ord-24990729b78942679a7dd6211d4a92c9
出典データセット
uspto-grants-1987_06
特許番号
US04677155

関連ノート

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