Ethylene Glycol → HCID 22322568, compound

HRID 902225Notes

Reaction equation

HRID 902225 reaction equation
[CH3:1][C:2]([CH3:10])([CH:8]=[O:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.CCOCC>[CH3:1][C:2]([CH3:10])([CH:8]1[O:13][CH2:12][CH2:11][O:9]1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 12647189HCID 12647189, compound

Product 1

HCID 22322568HCID 22322568, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl 3,3-dimethyl-4-oxobutanoate (10 g, 70 mmol), prepared according to the procedure of Hudlicky et al., Synth. Commun., 16 169 (1986), was dissolved in 40 mL of benzene, followed by addition of ethylene glycol (20 mL), and p-toluenesulfonic acid monohydrate (1.3 g). The reaction was refluxed with azeotropic removal of water for 1 hour. The reaction was poured into 200 mL of ether, washed with saturated sodium bicarbonate, water and brine, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to give 12.4 g (94%) of the title compound.

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f010095d4f04e3d856a433bc00b4c16
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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