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

HRID 36561
Notes
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Reaction equation

HRID 36561 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d58fcbdd740644d9af498b7e9b6eb406
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05416061

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes