Nitric Acid → HCID 57756017, compound

HRID 227356Notes

Reaction equation

HRID 227356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[O:7].[N+:13]([O-])([OH:15])=[O:14]>>[CH3:12][O:11][C:9]1[C:8]([N+:13]([O-:15])=[O:14])=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1)[CH:6]=[O:7]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 57756017HCID 57756017, compoundYield 64%

Procedure

The 3,5-Dimethoxybenzaldehyde (0.5 g, 3 mmol) was added to 70% nitric acid (0.88 mL, 14.44 mmol) at 0° C. in portion. After stirring for 1 hour, the reaction mixture was quenched and extracted by water and CH2Cl2. The organic layers were combined and evaporated to give a residue, which was purified by flash chromatography (EtOAc:n-hexane=1:2.5) to give the brown crystals, yield 64%. mp 104.0-104.6° C., 1H NMR (500 MHz, CDCl3) δ 3.93 (s, 3H), 3.93 (s, 3H), 6.76 (d, J=2.4 Hz), 6.96 (d, J=2.4 Hz, 1H), 9.94 (s, 1H).

Workup

  1. customthe reaction mixture was quenched
  2. extractionextracted by water and CH2Cl2
  3. customevaporated
  4. customto give a residue, which
  5. customwas purified by flash chromatography (EtOAc:n-hexane=1:2.5)
  6. customto give the brown crystals, yield 64%

Sources & evidence

ORD record
ord-d4156ce379b640d7905c7057bf13aca0
Source dataset
uspto-grants-2009_07
Patent number
US07560491B2

Reaction notes

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