Hydrochloric Acid → 5-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acid

HRID 35265Notes

Reaction equation

HRID 35265 reaction equation
Cl.[C:2]1([N:8]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[N:11][N:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[C:2]1([N:8]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[N:11][N:10]=[N:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21295291Methyl 5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valerate

Product 1

HCID 142300655-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20% aqueous Hydrochloric acid (100 ml) is added to methyl 5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valerate (9.3 g) and the mixture is refluxed for 4 hours. After cooling, water is added and the mixture is extracted with chloroform. The chloroform solution is extracted with aqueous saturated sodium bicarbonate solution. The aqueous layer is acidified with concentrated hydrochloric acid and again extracted with chloroform. The latter chloroform extract is washed with aqueous saturated sodium chloride solution and dried over magnesium sulfate. Chloroform is distilled off to give 5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valeric acid (8.2 g), pale yollow liquid.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with chloroform
  4. extractionThe chloroform solution is extracted with aqueous saturated sodium bicarbonate solution
  5. extractionagain extracted with chloroform
  6. extractionThe latter chloroform extract
  7. washis washed with aqueous saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. distillationChloroform is distilled off

Sources & evidence

ORD record
ord-c39aeef6379a4751b6593f403ab2037e
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Reaction notes

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