Carbon Dioxide → 1,2-Ethanediol, 1-(4-nitrobenzoate)

HRID 1761988Notes

Reaction equation

HRID 1761988 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][O:2]1.[N+:7]([C:10]1[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=1)([O-:9])=[O:8].C(=O)=O>[Cl-].C([N+](CC)(CC)CC)C.C(OCC)(=O)C>[OH:5][CH2:4][CH2:3][O:2][C:1](=[O:6])[C:13]1[CH:17]=[CH:18][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 61084-Nitrobenzoic AcidHCID 7303Ethylene carbonate

Product 1

HCID 111173351,2-Ethanediol, 1-(4-nitrobenzoate)

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

Ethylene carbonate (20 g., 0.22 mole), 4-Nitrobenzoic acid (38 g., 0.2 mole), and tetraethylammonium chloride (2.0 g., 0.04 mole) were placed in a one liter round bottom flask and heated at 140° C. with stirring until evolution of CO2 stopped. The reaction was cooled to room temperature and dissolved in one liter of ethyl acetate. The solution was washed with water and dried over MgSO4. The drying agent was removed by filtration. The volume was reduced in-vacuo and the 2-hydroxyethyl-4-nitrobenzoate obtained as a pale yellow solid. The structure was confirmed by NMR spectroscopy.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe solution was washed with water
  3. dry with materialdried over MgSO4
  4. customThe drying agent was removed by filtration

Sources & evidence

ORD record
ord-5293ba7d4f2d47639cdab9751b864037
Source dataset
uspto-grants-1989_05
Patent number
US04829099

Reaction notes

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