Hydrochloric Acid → 1,8-Dichloro-10-[Bis(Ethoxycarbonyl)Methylene]-Anthrone

HRID 364873

反応式

HRID 364873 の反応式
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:17])[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(Cl)Cl.Cl>[Ti](Cl)(Cl)(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:17])[C:7](=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([O:27][CH2:28][CH3:29])=[O:26])[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67081,8-DichloroanthraquinoneHCID 7761Diethyl Malonate

生成物 1

HCID 136688941,8-Dichloro-10-[Bis(Ethoxycarbonyl)Methylene]-Anthrone

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 1049Pyridine溶媒

実験手順

In a 250 milliliter round-bottomed flask equipped with a pressure equalizing dropping funnel, there was discharged 10 grams of 1,8-dichloroanthraquinone, 16.5 milliliters of diethyl malonate, and 150 milliliters of methylene chloride under a nitrogen atmosphere. The resulting mixture was then mechanically stirred and cooled with an ice bath. Thereafter, 24 milliliters of titanium tetrachloride was added dropwise through the dropping funnel over a period of 20 minutes, followed by the addition of 45 milliliters of pyridine. The reaction mixture was then stirred at room temperature for 65 hours. Subsequently, 150 milliliters of a dilute aqueous hydrochloric acid solution was slowly added with stirring. The organic phase resulting was separated, washed twice with water, and dried with anhydrous magnesium sulfate. Evaporation of the dried organic solution yielded a yellowish solid which when recrystallized from methanol afforded 7.5 grams of the pure Compound (VIII), mp., 166°-167° C.

後処理

  1. customIn a 250 milliliter round-bottomed flask equipped with a pressure
  2. temperaturecooled with an ice bath
  3. stirringThe reaction mixture was then stirred at room temperature for 65 hours
  4. stirringwith stirring
  5. customThe organic phase resulting
  6. customwas separated
  7. washwashed twice with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customEvaporation of the dried organic solution
  10. customyielded a yellowish solid which when
  11. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-7d60987053a147c5aa1b4fb13934411e
出典データセット
uspto-grants-1986_08
特許番号
US04606861

関連ノート

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