Hydrochloric Acid → HCID 21105758, compound

HRID 1354450Notes

Reaction equation

HRID 1354450 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.P([O-])(O)(O)=[O:25].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl>O1CCCC1.C(O)(C)(C)C.O>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([C:18]([OH:25])=[O:19])=[CH:16][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 184469834-{5-[4-(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 21105758HCID 21105758, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-[5-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (1.30 g), sodium dihydrogen phosphate (0.51 g), 2-methyl-2-butene (1.3 ml), water (15 ml), t-butanol (15 ml) and tetrahydrofuran (30 ml) was slowly added sodium chlorite (0.75 g) at 0° C., and the mixture was stirred for 2 hrs. To the reaction mixture was added conc. hydrochloric acid (3 ml), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained colorless crystals were recrystallized from tetrahydrofuran-hexane to give 4-[5-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl]benzoic acid (1.21 g, yield 89%). melting point: 286–287° C.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained colorless crystals were recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-dd6364c20c7145d7a3780f834e7d10bb
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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