Ethylene Glycol → 4-(2-Methyl-1,3-dioxolan-2-yl)-2-butanone

HRID 1816944Notes

Reaction equation

HRID 1816944 reaction equation
[CH3:1][C:2](=[O:8])[CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[CH2:9](O)[CH2:10][OH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:6][C:5]1([CH2:4][CH2:3][C:2](=[O:8])[CH3:1])[O:11][CH2:10][CH2:9][O:7]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 80352,5-Hexanedione

Product 1

HCID 5383774-(2-Methyl-1,3-dioxolan-2-yl)-2-butanone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A commercially available hexan-2,5-dion (137 g) was dissolved in benzene (300 ml). Thereafter, ethylene glycol (100 ml) and p-toluenesulfonic acid (11.4 g) were added to the solution, and the mixture was then dehydrated by heating to reflux for 5 hours. The reaction product was diluted with ethyl acetate, and then washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution. The organic layer was then dried over anhydrous sodium sulfate. The solvent was-distilled off under a reduced pressure, and the residue was subjected to vacuum distillation (80° C. to 82° C./3 mmHg) to obtain 4-(2-methyl[1,3]dioxolan-2-yl)butan-2-one (56.83 g).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 5 hours
  3. washwashed with an aqueous saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. distillationThe solvent was-distilled off under a reduced pressure
  6. distillationthe residue was subjected to vacuum distillation (80° C. to 82° C./3 mmHg)

Sources & evidence

ORD record
ord-d755808fcb0241f0974b2c260c0b9545
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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