Water → 4-Cyanobenzoic acid

HRID 2304081Notes

Reaction equation

HRID 2304081 reaction equation
[C:1](#[N:10])[C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.[OH-:11].[Na+].[OH2:13]>C(O)(C)(C)C>[C:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:13])=[O:11])=[CH:4][CH:3]=1)#[N:10]

Participants

5

Reactant 3

HCID 962WaterHCID 121721,4-DicyanobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 120874-Cyanobenzoic acidYield 120.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
5 °C

Procedure

Terephthalonitrile (12.8 g), sodium hydroxide (2.4 g), water (1.5 g), tert-butyl alcohol (300 ml) were mixed, and the resultant mixture stirred vigorously at 80° C. After the solvent was removed through distillation, sodium nitrite (16.6 g), acetic acid (250 ml), and acetic anhydride (25 ml) were added to the residue, and the resultant mixture was stirred vigorously at 5° C. Trifluoroacetic acid (27 g) was added dropwise to the mixture over three hours, and the mixture was further stirred vigorously for five hours. The solvent was removed through distillation under reduced pressure, and water (500 ml) was added to the residue. Sodium hydroxide was added to the solution under cooling with ice so as to adjust the pH to 8. After insoluble matter was removed through filtration, concentrated sulfuric acid was added to the filtrate under cooling with ice so as to adjust the pH to 4. Precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 10.6 g of p-cyanobenzoic acid (yield 72%). The obtained p-cyanobenzoic acid had a purity of 95%.

Workup

  1. customAfter the solvent was removed through distillation, sodium nitrite (16.6 g), acetic acid (250 ml), and acetic anhydride (25 ml)
  2. additionwere added to the residue
  3. additionTrifluoroacetic acid (27 g) was added dropwise to the mixture over three hours
  4. stirringthe mixture was further stirred vigorously for five hours
  5. customThe solvent was removed through distillation under reduced pressure, and water (500 ml)
  6. additionwas added to the residue
  7. additionSodium hydroxide was added to the solution
  8. temperatureunder cooling with ice so as
  9. customAfter insoluble matter was removed through filtration, concentrated sulfuric acid
  10. additionwas added to the filtrate
  11. temperatureunder cooling with ice so as
  12. customPrecipitated crystals
  13. filtrationwere collected through filtration
  14. washwashed with water
  15. customdried

Sources & evidence

ORD record
ord-c6b09c3163d040c08c90b00b24db0730
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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