Ethylene Glycol → Methyl 4,4-ethylenedioxy-3-methyl-butanoate

HRID 2051726Notes

Reaction equation

HRID 2051726 reaction equation
[CH3:1][CH:2]([CH:8]=[O:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>CCOCC>[CH2:10]1[CH2:11][O:12][CH:8]([CH:2]([CH3:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[O:9]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 11804788Methyl 3-methyl-4-oxobutanoate

Product 1

HCID 20305753Methyl 4,4-ethylenedioxy-3-methyl-butanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-methyl-4-oxo-butanoate (86.3 g), ethylene glycol (61.75 g, 0.996 m), p-toluenesulfonic acid (1 g) and benzene (700 ml) is refluxed under nitrogen for 16 hr. The resulting mixture is allowed to cool to room temperature and treated with ether (300 ml). The organic phase is washed with 5% sodium bicarbonate solution (100 ml), dried (Na2SO4) and evaporated in vacuo to give methyl 4,4-ethylenedioxy-3-methyl-butanoate as a crude product (63.2 g). This material is used directly in the next step.

Workup

  1. temperatureis refluxed under nitrogen for 16 hr
  2. washThe organic phase is washed with 5% sodium bicarbonate solution (100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c30988f0051a47189587616052ccb2d1
Source dataset
uspto-grants-1980_01
Patent number
US04182717

Reaction notes

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