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

HRID 1386942Notes

Reaction equation

HRID 1386942 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=1.[CH2:13](O)[CH2:14][OH:15].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[O:15][CH2:14][CH2:13][O:11]2)[CH:5]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 639145Methyl 3-formylbenzoate

Product 1

HCID 19102594Methyl 3-(1,3-dioxolan-2-yl)benzoateYield 101%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-formyl-benzoic acid methyl ester (9.48 g, 57.8 mmol), ethylene glycol (8.97 g, 144.5 mmol, 2.5 eq.) and conc. sulfuric acid (0.18 g, 1.8 mmol) in toluene was heated under Dean-Stark reflux for 3 hrs. After cooling, satd. NaHCO3 (100 ml) was added. The aqueous phase was extracted with EtOAc, the combined organic phases were dried over Na2SO4 and evaporated to afford the title compound (12.1 g, 101% yield) as a yellow liquid. MS: m/e=164 (M+).

Workup

  1. temperaturereflux for 3 hrs
  2. temperatureAfter cooling
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-e39da316feef42a8ad66754bd909f4f8
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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