Acetone → 1,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

HRID 2372408Notes

Reaction equation

HRID 2372408 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5])[CH3:2].[CH3:10][C:11]([CH3:13])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:10][C:11]1([CH3:13])[O:7][CH2:6][C:3]([CH2:1][CH3:2])([CH2:8][OH:9])[CH2:4][O:5]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 6510Trimethylolpropane

Product 1

HCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Ethyl-2-hydroxymethyl-propan-1,3-diol (34 g.), acetone (37 ml.) and p-toluenesulphonic acid (0.5 g.) were refluxed in benzene (140 ml.) and water was removed using Dean and Stark apparatus. After ten hours refluxing the mixture was cooled and washed with saturated aqueous sodium hydrogen carbonate solution. The benzene solution was dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. Distillation gave 2,2-dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane (35 g.), a colourless oil (bpt) 80°-2° 0.9 mm)2.

Workup

  1. customwater was removed
  2. temperatureAfter ten hours refluxing the mixture
  3. temperaturewas cooled
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe benzene solution was dried over anhydrous magnesium sulphate
  6. customThe solvent was removed in vacuo
  7. distillationDistillation

Sources & evidence

ORD record
ord-dc98acead3a04c14a9822474d6d49580
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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