1-Propanol → n-Propyl-4-chloro-3,5-dinitro-benzoate

HRID 1382132Notes

Reaction equation

HRID 1382132 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].S(=O)(=O)(O)O.[CH2:22](O)[CH2:23][CH3:24]>C1C=CC=CC=1.O>[CH2:22]([O:7][C:6](=[O:8])[C:5]1[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([Cl:1])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=1)[CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 10311-Propanol2×HCID 1118Sulfuric AcidHCID 83774-Chloro-3,5-dinitrobenzoic acid

Product 1

HCID 85970396n-Propyl-4-chloro-3,5-dinitro-benzoateYield 88%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

Into a 50 l enamelled double-walled apparatus equipped with a stirrer and adjusted to azeotropic distillation 7.5 kg (0.125 kmole) of n-propanol, 19 kg of benzene, 25 kg (0.1 kmole) of 4-chloro-3,5-dinitro-benzoic acid and 1 kg of concentrated sulfuric acid are weighed in. The reactor is closed and the content thereof is heated to boiling by means of steam heating. The reaction mixture is heated to boiling (86°-90° C. until no more water leaves the system while the organic phase (a mixture of benzene and n-propanol) is continuously reintroduced into the reactor. Once the distillation of water is completed (5-7 hours) the mixture is cooled below 20° C., the precipitated crystals are isolated by centrifugation, washed with cold benzene and dried. Thus 25.4 kg of the desired compound are obtained, yield 88%, purity 97%.

Workup

  1. customequipped with a stirrer
  2. customThe reactor is closed
  3. temperaturethe content thereof is heated
  4. temperatureheating
  5. temperatureThe reaction mixture is heated
  6. custom86°-90° C.
  7. customleaves the system while the organic phase (
  8. additionis continuously reintroduced into the reactor
  9. distillationOnce the distillation of water
  10. custom(5-7 hours)
  11. temperatureis cooled below 20° C.
  12. customthe precipitated crystals are isolated by centrifugation
  13. washwashed with cold benzene
  14. customdried

Sources & evidence

ORD record
ord-487da84140f8422295b226986c8e9b22
Source dataset
uspto-grants-1989_02
Patent number
US04806151

Reaction notes

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