Hydrochloric Acid → 4-[5-(4-t-Butylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid

HRID 1354456Notes

Reaction equation

HRID 1354456 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)=[N:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[N:13][N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934530Methyl 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoate

Product 1

HCID 211057574-[5-(4-t-Butylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acidYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (0.600 g), 1 M aqueous sodium hydroxide solution (3.6 ml), tetrahydrofuran (6 ml) and ethanol (3 ml) was heated under reflux for 1.5 hrs. After cooling, 1 M hydrochloric acid was added to acidify the mixture. The crystals were collected by filtration to give 4-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.550 g, yield 95%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: 284–286° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hrs
  3. temperatureAfter cooling
  4. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-9de9f690d8ea4da5993d16d766eee467
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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