p-Toluenesulfonic acid → 5-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

HRID 1613096Notes

Reaction equation

HRID 1613096 reaction equation
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.[OH:12][CH2:13][C:14]([CH3:19])([CH2:17][OH:18])[CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:12][CH2:13][C:14]1([CH3:19])[CH2:17][O:18][C:1]([CH3:6])([CH3:2])[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6502TrimethylolethaneHCID 11430Potassium Carbonate

Product 1

HCID 3737095-Hydroxymethyl-2,2,5-trimethyl-1,3-dioxaneYield 8,383.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.0 g of p-toluenesulfonic acid is added to 96.2 g (0.80 mol) of 2-(hydroxymethyl)-2-methyl-1,3propanediol in 600 ml of acetone, and the mixture is heated to reflux. After 5 hours, the solution is neutralized while still hot by adding 3.0 g of potassium carbonate, and the mixture is stirred for a further 30 minutes and subsequently allowed to stand at room temperature overnight. The mixture is filtered through kieselguhr, and the solvent is removed by distillation in vacuo, leaving about 180 ml of a turbid, oily residue, which is purified by distillation in a high vacuum, giving 78 g of the alcohol 31 as a colorless, viscous oil.

Workup

  1. temperaturethe mixture is heated to reflux
  2. waitto stand at room temperature overnight
  3. filtrationThe mixture is filtered through kieselguhr
  4. customthe solvent is removed by distillation in vacuo
  5. customleaving about 180 ml of a turbid, oily residue, which
  6. distillationis purified by distillation in a high vacuum

Sources & evidence

ORD record
ord-8552753fc6b54646af519cc9c5edaed0
Source dataset
uspto-grants-1993_03
Patent number
US05191069

Reaction notes

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