Sodium Iodide → Allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylate

HRID 2225501Notes

Reaction equation

HRID 2225501 reaction equation
[I-:1].[Na+].S(O[CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:21])([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:11][CH2:10]1)(C)(=O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[I:1][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:21])([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 19004719Allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate

Product 1

HCID 19004693Allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylateYield 49.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g of sodium iodide was added to a solution of 2 g of allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate (Example 45) in 50 ml of acetone. The solution was reacted for 4 hours, while it was refluxed. After reaction, 100 ml of an aqueous sodium thiosulfate solution was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium thiosulfate solution and twice with an aqueous sodium chloride solution, and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 10 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 1.1 g of allyl 4-iodomethyl-1-methyl-1-cyclohexanecarboxylate as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 4 hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed twice with an aqueous sodium thiosulfate solution and twice with an aqueous sodium chloride solution
  7. dry with materialwas dried over magnesium sulfate
  8. customThereafter, the solvent was removed in vacuo
  9. customThe oily substance obtained
  10. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f37a82d7fe964bbfa9bde494268ab89c
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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