3-Nitrobenzaldehyde → 2-(3-nitrophenyl)-1,3-dioxolane

HRID 2117248Notes

Reaction equation

HRID 2117248 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[CH:12](O)([OH:14])[CH3:13]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]2[O:14][CH2:12][CH2:13][O:8]2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 1512111,1-Ethanediol

Product 1

HCID 2406102-(3-nitrophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Protection of the aldehyde was performed following reported procedures. (Borchardt, R. T.; Huber, J. A.; Houston, M. J. Med. Chem. 1982, 25, 258.; Brasili, L.; Sorbi, C.; Franchini, S.; Manicardi, M.; Angeli, P.; Marucci, G.; Leonarke, A.; Poggesi, E. J. Med. Chem. 2003, 46, 1504) 3-Nitrobenzaldehyde (4.0 g, 26.4 mmol) was dissolved in toluene (200 mL). Following this, ethanediol (3.0 mL, 53 mmol, 2.0 eq) was added to the solution and the resulting mixture was refluxed overnight with a Dean-Stark trap. The reflux mixture was then extracted with saturated NaHCO3 (2×75 mL). The organic layer was dried with Na2SO4 and concentrated under reduced pressure. The residue was then purified by flash column chromatography (30% EtOAc/hexanes) to afford 3-nitrophenyl-1,3-dioxolane as a clear yellow oil that solidified upon standing. (5.09 g, 98%, Rf=0.7 40% EtOAc/hexanes). 1H-NMR (400 MHz, CDCl3, δ): 4.0-4.2 (m, 4H), 5.87 (s, 1H), 7.55 (t, 1H, J=7.93 Hz), 7.79 (d, 1H, J=7.7 Hz), 8.21 (dd, 1H, J1=1.2 Hz, J2=8.2 Hz), 8.34 (s, 1H). 13C-NMR (100 MHz, CDCl3, δ): 148.4, 140.5, 132.8, 129.6, 124.1, 121.8, 102.3, 65.6.

Workup

  1. additionwas added to the solution
  2. temperaturethe resulting mixture was refluxed overnight with a Dean-Stark trap
  3. extractionThe reflux mixture was then extracted with saturated NaHCO3 (2×75 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was then purified by flash column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3abbade06ffa4a3fb59c36c148dc291f
Source dataset
uspto-grants-2008_10
Patent number
US07442529B2

Reaction notes

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