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

HRID 703143

反応式

HRID 703143 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24470Silver Nitrate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19c70a89ebce40fb8dafee85e0c5c210
出典データセット
uspto-grants-1991_01
特許番号
US04981874

関連ノート

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