Sulfuric Acid → trans-1-Iodo-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

HRID 27301Notes

Reaction equation

HRID 27301 reaction equation
Cl/[CH:2]=[CH:3]/[C:4]([C:6]1([CH3:12])[CH2:9][CH:8]([CH2:10][CH3:11])[CH2:7]1)=[O:5].[I-:13].[Na+].OS(O)(=O)=O>CC(C)=O>[I:13]/[CH:2]=[CH:3]/[C:4]([C:6]1([CH3:12])[CH2:9][CH:8]([CH2:10][CH3:11])[CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 23344457trans-1-Chloro-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

Product 1

HCID 23344489trans-1-Iodo-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-oneYield 108.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4.2 g of trans-1-chloro-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one (prepared in Example 5A) and 10 g of anhydrous sodium iodide in 60 ml of acetone was refluxed with about 0.5 ml H2SO4 for 4 hr under an argon atmosphere. The solvent was removed by evaporation in vacuo. The residue was diluted with water and the aqueous mixture was extracted several times with ether. The combined ether extract was washed with aqueous sodium thiosulfate solution and then dried over anhydrous magnesium sulfate and evaporated in vacuo to yield 6.8 g of the title compound having the following physical characteristics:

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. additionThe residue was diluted with water
  3. extractionthe aqueous mixture was extracted several times with ether
  4. extractionThe combined ether extract
  5. washwas washed with aqueous sodium thiosulfate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9e358ecf75f349d7ab8b62c8b55815e0
Source dataset
uspto-grants-1980_09
Patent number
US04220795

Reaction notes

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