Ethylene Glycol → HCID 71254747, compound

HRID 1396331Notes

Reaction equation

HRID 1396331 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 saturated NaHCO3 solution. The organic layer was dried (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 the desired product (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 saturated NaHCO3 solution
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a residue
  11. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4f03385083cc4a368ce136bf07bd8f21
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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