2-Chloro-1,4-naphthoquinone → 1,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

HRID 703143

반응식

HRID 703143 반응식
[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][CH:24](C(O)=O)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][CH:24]([C:11]3[C:10](=[O:12])[C:9]4[C:4]([C:3](=[O:13])[C:2]=3[Cl:1])=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1

참가 물질

7

반응물 3

HCID 138912-Chloro-1,4-naphthoquinoneHCID 62648Ammonium PersulfateHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

생성물 1

HCID 111010701,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-수율 35%

시약·촉매·용매 3

HCID 24470Silver Nitrate촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 2-chloro-1,4-naphthoquinone (3.95 g, 0.02 mol), 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid (4.9 g, 0.02 mol) and powdered silver nitrate (1.05 g. 0.0062 mol) was heated to reflux with vigorous stirring in 40 ml of acetonitrile. A solution of ammonium persulphate (12.0 g, 0.0525 mol) in 50 ml of water was added dropwise over 1 hour. The mixture was refluxed for 3 hours the cooled in ice for 30 mins, after which it was filtered, and the residual sticky solid extracted twice with boiling chloroform to remove inorganic material. The chloroform was removed by evaporation to leave a yellow-brown solid (ca 2.7 g). This was dissolved in 40 ml of boiling acetonitrile; a little insoluble material was removed by filtration.

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 3 hours the
  4. temperaturecooled in ice for 30 mins
  5. filtrationafter which it was filtered
  6. extractionthe residual sticky solid extracted twice with boiling chloroform
  7. customto remove inorganic material
  8. customThe chloroform was removed by evaporation

출처 및 근거

ORD 기록
ord-19c70a89ebce40fb8dafee85e0c5c210
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04981874

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