Hydrochloric Acid → 4-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid

HRID 1354454Notes

Reaction equation

HRID 1354454 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[C:1]1([C:7]2[O:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=3)=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934545HCID 22934545, compound

Product 1

HCID 5969954-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-[5-phenyl-1,3,4-oxadiazol-2-yl]benzoate (0.180 g), 1 M aqueous sodium hydroxide solution (1.3 ml), tetrahydrofuran (2 ml) and methanol (1 ml) was stirred at room temperature for 1 hr. and acidified by adding 1 M hydrochloric acid. The crystals were collected by filtration to give 4-[5-phenyl-1,3,4-oxadiazol-2-yl]benzoic acid (0.150 g, yield 88%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: >300° C.

Workup

  1. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-215a764ff1cb4202a9f2301acb851a25
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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