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

HRID 1732278Notes

Reaction equation

HRID 1732278 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 hours. 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-methylbutanoate as a crude product (63.2 g). This material is used directly in the next step.

Workup

  1. temperatureis refluxed under nitrogen for 16 hours
  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-4391e1b870f9420880c8af9d328f3771
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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