p-Toluenesulfonic acid → 1,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

HRID 1613093Notes

Reaction equation

HRID 1613093 reaction equation
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.[OH:12][CH2:13][C:14]([CH2:19][OH:20])([CH2:17][CH3:18])[CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:2][C:1]1([CH3:6])[O:16][CH2:15][C:14]([CH2:17][CH3:18])([CH2:19][OH:20])[CH2:13][O:12]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6510TrimethylolpropaneHCID 11430Potassium Carbonate

Product 1

HCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-Yield 8,050.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.75 g of p-toluenesulfonic acid are added to 275 g (2.05 mol) of 2,2-bis(hydroxymethyl)-1-butanol in 1.4 1 of acetone, and the mixture is heated to reflux. After 4 hours, the solution is neutralized while still hot by adding 8.25 g of potassium carbonate, and the mixture is stirred for a further 30 minutes and subsequently allowed to stand overnight at room temperature. The turbid mixture is filtered through kieselguhr, and the solvent is removed by distillation in vacuo, leaving 400 ml of a turbid, oily residue, which is purified by distillation in a high vacuum, giving 224 g of the alcohol 1 as a colorless oil.

Workup

  1. temperaturethe mixture is heated to reflux
  2. waitto stand overnight at room temperature
  3. filtrationThe turbid mixture is filtered through kieselguhr
  4. customthe solvent is removed by distillation in vacuo
  5. customleaving 400 ml of a turbid, oily residue, which
  6. distillationis purified by distillation in a high vacuum

Sources & evidence

ORD record
ord-3f393a2db6784422b9751eefd47bfa29
Source dataset
uspto-grants-1993_03
Patent number
US05191069

Reaction notes

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