Ethylene Glycol → HCID 71254747, compound

HRID 1481273Notes

Reaction equation

HRID 1481273 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])=[O:2].[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1.C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1>[O:2]1[CH2:16][CH2:17][O:18][CH:1]1[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Product 1

HCID 71254747HCID 71254747, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-formyl-3-nitrobenzoate (9.0 g, 43.0 mmol) in toluene (150 mL) was added ethylene glycol (7.20 mL, 129 mmol) followed by p-TsOH (0.409 g, 2.152 mmol) and the reaction mixture was heated at reflux temperature with azeotropic removal of H2O using a Dean-Stark trap for 4 h. The reaction mixture was then cooled and diluted with DCM. The DCM layer was then washed with sat. aq. NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated to yield a residue. The residue was dissolved in minimal quantity of DCM and purified by silica gel chromatography to yield 5A (8.53 g, 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.27 (d, J=8.2 Hz, 1H), 7.90 (d, J=8.2 Hz, 1H), 6.38 (s, 1H), 4.00 (dt, J=3.8, 1.9 Hz, 2H), 3.94 (dt, J=3.8, 1.9 Hz, 2H), 3.91 (s, 3H) ppm.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature
  3. customwith azeotropic removal of H2O using a Dean-Stark trap for 4 h
  4. temperatureThe reaction mixture was then cooled
  5. additiondiluted with DCM
  6. washThe DCM layer was then washed with sat. aq. NaHCO3
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a residue
  11. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-1001de00086940c8a63c4965565b950f
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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