Nitric Acid → 5-(Chloromethyl)-2-hydroxy-3-nitrobenzaldehyde

HRID 257687Notes

Reaction equation

HRID 257687 reaction equation
[Cl:1][CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[Cl:1][CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3352915-(Chloromethyl)-2-hydroxybenzaldehyde

Product 1

HCID 124049055-(Chloromethyl)-2-hydroxy-3-nitrobenzaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
30 °C

Procedure

179 g. (0.01 mole) of 5-chloromethylsalicylaldehyde, prepared according to Angyal, S. J. et al, J. Chem. Soc. 1950, 2145, was dissolved in 20 ml. of glacial acetic acid. To this solution there was added a solution of 0.63 g. fuming nitric acid in 10 ml. glacial acetic acid over 30 minutes, keeping the mixture at 30° C., followed by stirring at 30° C. for 2 hours. The solution was then poured over ice to give a precipitate which was crystallized from methylene chloride giving the title product. Another crop was obtained by extraction of the aqueous phase, drying with anhydrous sodium sulfate, evaporation and crystallization from methylene chloride. Total yield: 53%.

Workup

  1. dissolution1950, 2145, was dissolved in 20 ml
  2. additionTo this solution there was added a solution of 0.63 g
  3. customat 30° C.
  4. additionThe solution was then poured over ice
  5. customto give a precipitate which
  6. customwas crystallized from methylene chloride giving the title product
  7. customAnother crop was obtained by extraction of the aqueous phase
  8. dry with materialdrying with anhydrous sodium sulfate, evaporation and crystallization from methylene chloride

Sources & evidence

ORD record
ord-ea47ff33f2ff40328a7cc5f6132ad98c
Source dataset
uspto-grants-1993_11
Patent number
US05262890

Reaction notes

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