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2-Methyl-2-butanol → 1-(4-Chlorophenyl)-2-methyl-2-(2-methylpropionyl)cyclopropane

HRID 1769043
Notes
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Reaction equation

HRID 1769043 reaction equation
[C:1](O)(CC)(C)C.[H-].[Na+].[H][H].[I-].C[S+](C)(C)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[C:25]([CH3:31])[C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[CH:20][CH:19]=1>CN1C(=O)CCC1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]2[CH2:31][C:25]2([CH3:1])[C:26](=[O:30])[CH:27]([CH3:28])[CH3:29])=[CH:22][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 544081871-(4-Chlorophenyl)-2,4-dimethyl-1-penten-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 157646801-(4-Chlorophenyl)-2-methyl-2-(2-methylpropionyl)cyclopropane

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
50 °C

Procedure

185 ml of tert-amyl alcohol are added to a suspension of 61.3 g of sodium hydride in 200 ml of NMP heated to 50° C. so as to have a steady evolution of hydrogen. The solution obtained is cooled to 25° C. and 176 g of solid trimethylsulphoxonium iodide are added, followed by a solution of 162 g of 1-(4-chlorophenyl)-2,4-dimethyl-1-penten-3-one in 250 ml of NMP. The resulting mixture is heated at 60° C. for 30 min. The product obtained is left in the reaction mixture for the following stage.

Workup

  1. customThe solution obtained
  2. temperatureis cooled to 25° C.
  3. temperatureThe resulting mixture is heated at 60° C. for 30 min
  4. customThe product obtained
  5. waitis left in the reaction mixture for the following stage

Sources & evidence

ORD record
ord-4b52d5e65894473f8709d10e3a5a75a8
Source dataset
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05380741

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes