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

HRID 877321Notes

Reaction equation

HRID 877321 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=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.C(OCC)(=O)C>[O:15]1[CH2:14][CH2:13][O:16][CH:1]1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 639145Methyl 3-formylbenzoate

Product 1

HCID 19102594Methyl 3-(1,3-dioxolan-2-yl)benzoateYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-formylbenzoate (2.5 g, 15.2 mmol), ethylene glycol (4.2 mL, 75 mmol) and para-toluenesulfonic acid monohydrate (0.29 g, 1.52 mmol) in toluene (60 mL) was heated at reflux under Dean and Stark conditions for 4 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with saturated sodium hydrogen carbonate and brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the title compound (3.09 g, 98%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under Dean and Stark conditions for 4 hours
  3. washwashed sequentially with saturated sodium hydrogen carbonate and brine
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-5976507e569648cb8c3fa9244695bd08
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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