Acetic Acid → 2,5-Dimethyl-3-nitrobenzaldehyde

HRID 326114Notes

Reaction equation

HRID 326114 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([CH3:13])=[CH:6][C:3]=1[CH2:4]Cl.C(O)(=[O:16])C.C1N2CN3CN(C2)CN1C3.Cl>O>[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([CH3:13])=[CH:6][C:3]=1[CH:4]=[O:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 156185981-(Chloromethyl)-2,5-dimethyl-3-nitrobenzene

Product 1

HCID 128316812,5-Dimethyl-3-nitrobenzaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The mixture constituted by 2,5-dimethyl-3-nitrobenzyl-chloride (A) prepared according to M. J. Winchester and F. D. Popp, J. Het. Chem. 12, p. 547 (1975) (610 g), acetic acid (1280 ml, water (1280 ml) and hexamethylene tetramine (855 g) was heated with reflux under stirring for 2 hours. 1037 ml of concentrated hydrochloric acid were then added in 10 minutes and the mixture was again heated with reflux for 20 minutes. This mixture, cooled to 0° C., gave a solid which was filtered off, dried and recrystallised from cyclohexane (4 liters) to give 290.5 g (53%) of yellow needles corresponding to the aldehyde of formula B, melting point: =90°-93° C.

Workup

  1. customprepared
  2. temperaturewith reflux
  3. temperaturethe mixture was again heated
  4. temperaturewith reflux for 20 minutes
  5. customgave a solid which
  6. filtrationwas filtered off
  7. customdried
  8. customrecrystallised from cyclohexane (4 liters)

Sources & evidence

ORD record
ord-7f8498d797f44493bd30385ca08012a2
Source dataset
uspto-grants-1984_04
Patent number
US04444776

Reaction notes

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