p-Toluenesulfonic acid → HCID 19373383, compound

HRID 1197351Notes

Reaction equation

HRID 1197351 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-toluenesulphonic 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-5b52f821d95841ae8f135fba8d55b9e2
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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