2-Methoxypropene → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 228929Notes

Reaction equation

HRID 228929 reaction equation
[CH3:1][O:2][C:3]([CH3:5])=[CH2:4].[OH:6][CH2:7][CH:8](CO)[CH2:9][OH:10]>CN(C)C=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:4][C:3]1([CH3:5])[O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:1][O:2]1

Participants

5

Reactant 2

HCID 83002-MethoxypropeneHCID 78432Trimethylolmethane

Product 1

HCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolYield 55%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methoxypropene (1 g) in N,N-dimethylformamide (150 ml) was added to 2-(hydroxymethyl)-1,3-propanediol (500 mg). p-Toluenesulfonic acid (10 mg) was added thereto, and the mixture was stirred at room temperature overnight. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with n-butanol. The n-butanol layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone to give (2,2-dimethyl[1,3]dioxan-5-yl)-methanol (378 mg, yield 55%).

Workup

  1. customThe solvent was removed by distillation under the reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with n-butanol
  4. washThe n-butanol layer was then washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-286338b454554e4489efeb880c1dd36b
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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