Acetone → Solketal

HRID 1712854Notes

Reaction equation

HRID 1712854 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH3:7][C:8]([CH3:10])=O.CS(O)(=O)=O>C1(C)C=CC=CC=1>[OH:1][CH2:2][CH:3]1[CH2:5][O:6][C:8]([CH3:10])([CH3:7])[O:4]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 753GlycerolHCID 6395Methanesulfonic Acid

Product 1

HCID 7528SolketalYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Glycerin (250 g), acetone (522 g) and 800 mL of toluene were charged into a 2 L four-neck flask to which a thermometer, a nitrogen inlet tube, a stirrer and a dehydrating column with a condenser were attached, and then, methane sulfonic acid (26 g) was added thereto and refluxed for 30 hours while removing the distilled water. Next, a potassium hydroxide solution was added to neutralize the reaction mixture. The reaction product was washed with ion exchanged water five times, and after that, the toluene was distilled off under reduced pressure, and thus, 298 g of 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolan was obtained.

Workup

  1. customa dehydrating column with a condenser were attached
  2. temperaturerefluxed for 30 hours
  3. customwhile removing the distilled water
  4. additionNext, a potassium hydroxide solution was added
  5. washThe reaction product was washed with ion
  6. distillationafter that, the toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fbee7b4c3e9145ffb89bb57aef18f9f1
Source dataset
uspto-grants-2010_09
Patent number
US07794619B2

Reaction notes

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