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

HRID 36561
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HRID 36561 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2회HCID 31358DimedoneHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d58fcbdd740644d9af498b7e9b6eb406
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05416061

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