p-Toluenesulfonic acid → 3-(2,2-Dimethyl-1,3-dioxolan-4-yl)propan-1-ol

HRID 1787056Notes

Reaction equation

HRID 1787056 reaction equation
[CH2:1]([OH:8])[CH:2]([OH:7])[CH2:3][CH2:4][CH2:5][OH:6].CO[C:11](OC)([CH3:13])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:12][C:11]1([CH3:13])[O:7][CH:2]([CH2:3][CH2:4][CH2:5][OH:6])[CH2:1][O:8]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 85763(+-)-1,2,5-Pentanetriol

Product 1

HCID 2315513-(2,2-Dimethyl-1,3-dioxolan-4-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Pentane-1,2,5-triol (5.00 g) was dissolved in acetone (150 mL), 2,2-dimethoxypropane (10.5 mL) and 4-methylbenzenesulfonic acid (794 mg) were added, and the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50) to give the title compound (3.79 g) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was separated
  3. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50)

Sources & evidence

ORD record
ord-727036fe3ce147629a7effcd602129c3
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

Loading…