Isopropanol → 3-phenylthiophene-2-carboxylic Acid

HRID 1611601Notes

Reaction equation

HRID 1611601 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]1([C:20]2[CH:24]=[CH:23][S:22][C:21]=2[CH:25]=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(C)C>CC(C)=O>[C:14]1([C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:25]([OH:3])=[O:26])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8188473-Phenyl-2-thiophenecarboxaldehydeHCID 131709961Jones' reagent

Product 1

HCID 25176253-phenylthiophene-2-carboxylic AcidYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8N Jones' reagent (ca. 10 ml) was added dropwise to a solution of 3-phenylthiophen-2-aldehyde (5) (0.58 g, 3.1 mmol) in 32 ml of acetone, until an orange colour persisted. The mixture was stirred at room temperature for 18 hrs. Isopropanol (5 ml) was added to remove the excess Jones' reagent and the mixture was then filtered, the organic solvents were evaporated under vacuum and extracted with ethyl acetate (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was then chromatographed using 95/5 chloroform/methanol, thus giving the compound (6) (0.44 g, 1.36 mmol, 46% yield) (M. Pt. 200–202° C.). 1H-NMR (CDCl3) ä 6.87–7.37 (m, 5H, Ph-H) 7.05 (d J=5.0 Hz, 1H, th-H4), 7.53 (d J=5.0 Hz, 1H, th-H5).

Workup

  1. customto remove the excess Jones' reagent
  2. filtrationthe mixture was then filtered
  3. customthe organic solvents were evaporated under vacuum
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. washThe combined organic layer was washed with a saturated solution of NaCl
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe mixture was then chromatographed

Sources & evidence

ORD record
ord-ba4876600699418ab19322d3af3c4d4f
Source dataset
uspto-grants-2006_01
Patent number
US06989388B2

Reaction notes

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