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Acetone Cyanohydrin → 2-(4-Methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione

HRID 36561
ノート
印刷プレビュー

反応式

HRID 36561 の反応式
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:24][C:25]1([CH3:33])[CH2:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[CH2:26]1.CC(C)(O)C#N>ClCCl>[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([CH:28]2[C:29](=[O:31])[CH2:30][C:25]([CH3:33])([CH3:24])[CH2:26][C:27]2=[O:32])=[O:10])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 31358DimedoneHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chloride

生成物 1

HCID 199371392-(4-Methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione収率 48.8%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A solution of 4-methylsulphonyl-2-nitrobenzoyl chloride (9.62 g) in dry dichloromethane (50 ml) was added to a stirred solution of triethylamine (5.6 ml) and 5,5-dimethylcyclohexane-1,3-dione (5 g) in dry dichloromethane (70 ml) during 30 minutes and the reaction mixture stirred at ambient temperature for 4 hours. Triethylamine (15.3 ml) and acetone cyanohydrin (0.5 ml) were added successively and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml), dried over magnesium sulphate and evaporated under reduced pressure to give a yellow glass which was recrystallised from methanol (20 ml) to give 2-(4-methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione (6.4 g), m.p. 156.5°-158° C., as a yellow crystalline solid.

後処理

  1. stirringthe reaction mixture stirred at ambient temperature for 18 hours
  2. washThe reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow glass which
  6. customwas recrystallised from methanol (20 ml)

出典と根拠

ORDレコード
ord-d58fcbdd740644d9af498b7e9b6eb406
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05416061

反応ノート

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