Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Methyl-2-butene | HCID 10553 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | HCID 21105734 | HCID 21105734 | — |
| Reactant | Sodium Chlorite | HCID 23668197 | — |
| Reactant | Monosodium phosphate | HCID 23672064 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21105735 | HCID 21105735 | 87.3% |
Reaction Steps
To a mixture of 3-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde (0.800 g), sodium dihydrogen phosphate (0.300 g), 2-methyl-2-butene (1.2 ml), t-butanol (10 ml), tetrahydrofuran (20 ml) and water (10 ml) was added sodium chlorite (0.570 g) at 0° C., and the mixture was stirred for 2 hrs. To the mixture was added aqueous sodium sulfite solution, and the mixture was stirred at room temperature for 30 min., acidified by adding 1 M hydrochloric acid, and extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 3-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]benzoic acid (0.730 g, yield 87%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: 239–240° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07223791B2 |
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| Source dataset | uspto-grants-2007_05 |
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| ORD ID | ord-cf39dd326a16413ebfb8d78fa278bac7 |
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| Source note | uspto-grants-2007_05 |
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