Benzene → n-Propyl-4-chloro-3,5-dinitro-benzoate

HRID 1382131Notes

Reaction equation

HRID 1382131 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].C1C=CC=CC=1.[Cl:11][C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][C:13]=1[N+:24]([O-:26])=[O:25].S(=O)(=O)(O)O>O>[CH2:1]([O:4][C:16](=[O:17])[C:15]1[CH:14]=[C:13]([N+:24]([O-:26])=[O:25])[C:12]([Cl:11])=[C:20]([N+:21]([O-:23])=[O:22])[CH:19]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10311-PropanolHCID 1118Sulfuric AcidHCID 83774-Chloro-3,5-dinitrobenzoic acid

Product 1

HCID 85970396n-Propyl-4-chloro-3,5-dinitro-benzoateYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1000 ml round-bottomed flask equipped with a stirrer, thermometer and Marcusson-condenser 180 g (3 moles) of n-propanol, and 380 g of benzene are weighed in, whereupon 493 g (2 moles) of 4-chloro-3,5-dinitro-benzoic acid and 20 g of concentrated sulfuric acid are added under stirring. The reaction mixture is heated to boiling on a water bath under stirring (86° C.) until no more water is distilled off. The water thus formed is collected in the Marcusson-condenser and removed if necessary. In the meantime the upper benzene/n-propanol phase is continuously re-introduced into the flask. The reaction having been completed the mixture is cooled to room temperature under stirring, the precipitated crystals are filtered off, washed with cold n-propanol and dried. Thus 490 g of the desired compound are obtained, yield 85%, purity 98%.

Workup

  1. customInto a 1000 ml round-bottomed flask equipped with a stirrer
  2. temperatureThe reaction mixture is heated
  3. customto boiling on a water bath
  4. distillationis distilled off
  5. customThe water thus formed
  6. customis collected in the Marcusson-condenser
  7. customremoved if necessary
  8. additionIn the meantime the upper benzene/n-propanol phase is continuously re-introduced into the flask
  9. stirringunder stirring
  10. filtrationthe precipitated crystals are filtered off
  11. washwashed with cold n-propanol
  12. customdried

Sources & evidence

ORD record
ord-01d7cf7891104beeae15bd179b44c3ec
Source dataset
uspto-grants-1989_02
Patent number
US04806151

Reaction notes

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