Ethylene Glycol → HCID 774818, compound

HRID 874814Notes

Reaction equation

HRID 874814 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH2:13]([OH:16])[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:15]1[CH2:14][CH2:13][O:16][CH:1]1[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 15294Methyl 4-FormylbenzoateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 774818HCID 774818, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To stirred solution of methyl 4-formylbenzoate (5.0 g, 30.46 mmol) in toluene (196 mL) was added ethylene glycol (8.49 mL, 152.3 mmol) and para-toluenesulfonic acid monohydrate (0.58 g, 3.05 mmol). The reaction mixture was heated at reflux under Dean and Stark conditions for 1.5 hours. The solvent was evaporated at reduced pressure and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic phase was removed and washed with further saturated aqueous sodium hydrogen carbonate, brine and dried (magnesium sulfate). The mixture was filtered and the solvent evaporated at reduced pressure to afford the title compound (6.29 g, 99%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under Dean and Stark conditions for 1.5 hours
  3. customThe solvent was evaporated at reduced pressure
  4. customthe residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  5. customThe organic phase was removed
  6. washwashed with further saturated aqueous sodium hydrogen carbonate, brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationThe mixture was filtered
  9. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-ebcb3d444d8c47d0a628200ec63defdd
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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