Glycerol → 1,3-Dioxolane-4-methanol, 2-methoxy-2-methyl-

HRID 1196689Notes

Reaction equation

HRID 1196689 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:18]([O-])([O-])([O:20][CH3:21])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[OH:1][CH2:2][CH:3]1[CH2:5][O:6][C:18]([O:20][CH3:21])([CH3:19])[O:4]1

Participants

6

Reactant 4

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 536300401-Methoxyethane-1,1-diolate

Product 1

HCID 108880641,3-Dioxolane-4-methanol, 2-methoxy-2-methyl-Yield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1-liter round-bottomed flask equipped with a pressure equalizing addition funnel was flushed with nitrogen and charged with 41.5 grams (451 mmol.) of glycerol, 750 ml. of methylene chloride and 100 mg. of p-toluenesulfonic acid. Methyl orthoacetate, 56.9 grams (473 mmol.), was added over 5 minutes at room temperature, with stirring; stirring was continued for 18 hours after which 1 gram of anhydrous sodium carbonate was added and the mixture was stirred for one additional hour and filtered. The solvent was stripped under vacuum to yield 65 grams (97% of theoretical) of 4-hydroxymethyl-2-methoxy-2-methyl-1,3-dioxolane as a clear oil. Its molecular structure was confirmed by proton and carbon-13 nuclear magnetic resonance spectroscopy.

Workup

  1. customA 1-liter round-bottomed flask equipped with a pressure
  2. additionaddition funnel
  3. customwas flushed with nitrogen
  4. stirringstirring
  5. stirringthe mixture was stirred for one additional hour
  6. filtrationfiltered

Sources & evidence

ORD record
ord-15ed432f74dc47d2b0741088204a06e1
Source dataset
uspto-grants-1992_05
Patent number
US05115042

Reaction notes

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