p-Toluenesulfonic acid → 5-t-Butyl-2,2-dimethyl-5-iodomethyl-1,3-dioxane

HRID 704136Notes

Reaction equation

HRID 704136 reaction equation
[C:1]([C:5]1([CH2:16][I:17])[CH2:10][O:9][C:8]2([CH2:15]CCC[CH2:11]2)[O:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[C:1]([C:5]1([CH2:16][I:17])[CH2:10][O:9][C:8]([CH3:15])([CH3:11])[O:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 200756033-t-Butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane)

Product 1

HCID 200755525-t-Butyl-2,2-dimethyl-5-iodomethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-t-butyl-3-iodomethyl-(1,5-dioxaspiro[5,5]undecane) (3.5 g.), p-toluenesulphonic acid (0.5 g.) and acetone (200 ml.) was refluxed for 36 hours. The mixture was cooled and sodium hydrogen carbonate (2.0 g.) was added. The solvent was removed in vacuo and the resulting oil was poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and then evaporated in vacuo. 5-t-Butyl-2,2-dimethyl-5-iodomethyl-1,3-dioxane was obtained as a colourless oil (2.3 g.) and was used without further purification.

Workup

  1. temperaturewas refluxed for 36 hours
  2. temperatureThe mixture was cooled
  3. customThe solvent was removed in vacuo
  4. additionthe resulting oil was poured into water
  5. extractionThe aqueous mixture was extracted with diethyl ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b0368d15037e44dd853648e2c77443a6
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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