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

HRID 1926143Notes

Reaction equation

HRID 1926143 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-7d52daa5c538410bb3fdf888d26db761
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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