Nitric Acid → 4-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde

HRID 2213835Notes

Reaction equation

HRID 2213835 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18]>ClCCCl>[Cl:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:17][CH3:18])=[CH:11][C:12]([CH:13]=[O:14])=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 107750234-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE

Product 1

HCID 219563824-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Fuming nitric acid (10 mL) is added dropwise to a −40° C. suspension of 5.00 g (23.36 mmol) of 4-(2-chloroethoxy)-3-methoxybenzaldehyde (Milbank, J. B. J., et. al., J. Med. Chem., 42(4), 649–658, 1999) in 23 mL of 1,2-dichloroethane. The reaction mixture is slowly allowed to warm to −10° C. The mixture is poured onto 300 mL of ice water and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the pale yellow solid is collected by filtration to provide 2.43 g (40%) of 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzaldehyde, mp 148–150° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether is added to the residue
  6. filtrationthe pale yellow solid is collected by filtration

Sources & evidence

ORD record
ord-328218e672dc469c9550b35cee734642
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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