Hydrochloric Acid → HCID 21105729, compound

HRID 1354462Notes

Reaction equation

HRID 1354462 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][CH:23]=[CH:22][C:17]=3[C:18]([O:20]C)=[O:19])=[N:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1.Cl>CO>[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][CH:23]=[CH:22][C:17]=3[C:18]([OH:20])=[O:19])=[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 21105767HCID 21105767, compound

Product 1

HCID 21105729HCID 21105729, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoate (1.50 g), 1 M aqueous sodium hydroxide solution (9.0 ml), tetrahydrofuran (18 ml) and methanol (9 ml) was heated under reflux for 1 hr. After cooling, 1 M hydrochloric acid was added to acidify the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 2-[5-(4-t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (1.26 g, yield 87%) as a colorless amorphous solid. NMR (CDCl3) δ: 1.35 (9H, s), 7.52 (2H, d, J=8.8 Hz), 7.67–7.76 (4H, m), 7.96–8.04 (3H, m), 8.15–8.20 (1H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2407763052ed4f288c148fe25dc6af35
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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