Nitric Acid → HCID 28690188, compound

HRID 2264495Notes

Reaction equation

HRID 2264495 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=[O:8])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>C(OCC)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[CH:7]=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2447283-Ethoxy-4-methoxybenzaldehyde

Product 1

HCID 28690188HCID 28690188, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-ethoxy-4-methoxybenzaldehyde (6.0 g, 33.3 mmol, 1.0 equiv; commercially available) in diethyl ether (50 mL) was added dropwise 65% nitric acid (4.12 mL, 5.81 g, 59.9 mmol, 1.8 equiv) over a period of 30 min at rt. After the addition was completed the reaction mixture was heated to reflux for 4 h. The reaction product precipitated out of solution, was filtered off, washed with cold diethyl ether (3×20 mL) and dried yielding 5.85 g (78%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.53 (t, J=7.0 Hz, 3H), 4.04 (s, 3H), 4.26 (q, J=7.0 Hz, 2H), 7.37 (s, 1H), 7.61 (s, 1H), 10.40 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.34, 56.68, 65.35, 107.31, 110.48, 125.52, 143.56, 152.54, 152.70, 187.60. MS (ISP): 225.9 [M+H]+.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureto reflux for 4 h
  4. customThe reaction product precipitated out of solution
  5. filtrationwas filtered off
  6. washwashed with cold diethyl ether (3×20 mL)
  7. customdried

Sources & evidence

ORD record
ord-637f4c5517c14703952a6232a4e108ab
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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