Sulfuric Acid → HCID 21105734, compound

HRID 1354477Notes

Reaction equation

HRID 1354477 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:15][N:16]=2)[CH:9]=[CH:10][CH:11]=1.S(=O)(=O)(O)O>CC(C)=O>[F:26][C:23]([F:24])([F:25])[C:20]1[CH:21]=[CH:22][C:17]([C:14]2[O:13][C:12]([C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=3)[CH:2]=[O:1])=[N:16][N:15]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22934532HCID 22934532, compound

Product 1

HCID 21105734HCID 21105734, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[3-(1,3-dioxolan-2-yl)phenyl]-5-(4-trifluoromethylphenyl)-1,3,4-oxadiazole (4.10 g), 0.5 M sulfuric acid (30 ml) and acetone (100 ml) was heated under reflux for 1 hr. After cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. This solution 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]benzaldehyde (3.58 g, yield 99%). Recrystallization from hexane-ethyl acetate gave colorless-prism crystals. melting point: 129–130° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washThis solution was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6be33873d3134c4bb483c0c0439f95b9
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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