Acetone → 2,2-Dimethyl-4-vinyl-1,3-dioxolane

HRID 1375667Notes

Reaction equation

HRID 1375667 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH:3]=[CH2:4].[CH3:7][C:8]([CH3:10])=O.COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:7][C:8]1([CH3:10])[O:5][CH:2]([CH:3]=[CH2:4])[CH2:1][O:6]1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane2×HCID 103383-Butene-1,2-diol

Product 1

HCID 27350232,2-Dimethyl-4-vinyl-1,3-dioxolaneYield 57%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Butene-1,2-diol (5.00 g, 56.7 mmol), acetone (9.88 g, 170 mmol), 2,2-dimethoxy propane (17.7 g, 170 mmol), and p-toluene sulfonic acid (1.62 g, 8.5 mmol) were added to benzene (100 mL). After 16 hours of reflux, starting material was observed by TLC. 2,2-Dimethoxy propane (9.99 g, 95.1 mmol) and acetone (1.58 g, 27.3 mmol) were then added, followed by an additional 3 hour reflux. The mixture was washed with saturated aqueous NaHCO3 and extracted with EtOAc (3×40 mL). The organic extracts were dried over MgSO4, filtered, concentrated and purified by column chromatography (5% ethyl acetate in hexanes) to provide the titled compound (4.12 g, 57%) as a light yellow oil.

Workup

  1. temperatureAfter 16 hours of reflux
  2. temperaturereflux
  3. washThe mixture was washed with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc (3×40 mL)
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ef3a54aaf4fe436a9218e5a805da9058
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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