p-Toluenesulfonic acid → HCID 19373383, compound

HRID 129299Notes

Reaction equation

HRID 129299 reaction equation
[CH2:1]([C:5]([CH2:10][OH:11])([CH2:8][OH:9])[CH2:6][OH:7])[CH2:2][CH:3]=[CH2:4].[C:12]1(C)[CH:17]=CC(S(O)(=O)=O)=C[CH:13]=1>CC(C)=O>[CH2:1]([C:5]1([CH2:6][OH:7])[CH2:8][O:9][C:12]([CH3:17])([CH3:13])[O:11][CH2:10]1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19373408HCID 19373408, compound

Product 1

HCID 19373383HCID 19373383, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of crude 2-(but-3-enyl)-2-hydroxymethylpropan-1,3-diol (4.5 g), acetone (30 ml) and p-toluenesulfonic acid (0.25 g) was refluxed in a Dean and Stark apparatus for 7 hours. The mixture was cooled and washed with aqueous sodium hydrogen carbonate solution. The organic solution was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was chromatographed on silica, eluting with 1:4 diethyl ether: hexane. 5-(But-3-enyl)-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was obtained as a colourless oil (1.0 g).

Workup

  1. temperaturewas refluxed in a Dean and Stark apparatus for 7 hours
  2. temperatureThe mixture was cooled
  3. washwashed with aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic solution was dried over anhydrous magnesium sulphate
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica
  7. washeluting with 1:4 diethyl ether

Sources & evidence

ORD record
ord-520186636808461cb032df9b67d2bd72
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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