Sodium Iodide → 2,2-Dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane

HRID 704129Notes

Reaction equation

HRID 704129 reaction equation
CS(O)(=O)=O.[CH3:6][C:7]1([CH3:17])[O:12][CH2:11][C:10]([CH2:15][CH3:16])([CH2:13]O)[CH2:9][O:8]1.[I-:18].[Na+]>CC(CC)=O>[CH3:6][C:7]1([CH3:17])[O:12][CH2:11][C:10]([CH2:15][CH3:16])([CH2:13][I:18])[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 200755932,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methylsulphonate

Product 1

HCID 200756052,2-Dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,2-dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane methylsulphonate (6.0 g.) and sodium iodide (9.0 g.) in ethyl methyl ketone was refluxed, with stirring, for forty-eight hours. The solvent was removed in vacuo and the resulting oil was poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were washed with 5% aqueous sodium thiosulphate solution and then water. The ethereal extracts were dried over anhydrous magnesium sulphate and then evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with 1:10 ether: hexane. 2,2-Dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane was obtained as a colourless oil (5.0 g.)

Workup

  1. temperaturewas refluxed
  2. customThe solvent was removed in vacuo
  3. additionthe resulting oil was poured into water
  4. extractionThe aqueous mixture was extracted with ether
  5. washThe ethereal extracts were washed with 5% aqueous sodium thiosulphate solution
  6. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica
  9. washeluting with 1:10 ether

Sources & evidence

ORD record
ord-64484f69e5e94edea47317d300e93f8f
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

Loading…