Potassium Hydroxide → 5-Isopropylthiophene-3-carboxylic acid

HRID 235096Notes

Reaction equation

HRID 235096 reaction equation
[OH-:1].[K+].[CH:3]([C:6]1[S:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)([CH3:5])[CH3:4]>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[CH:3]([C:6]1[S:7][CH:8]=[C:9]([C:11]([OH:1])=[O:12])[CH:10]=1)([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 233535565-Isopropylthiophene-3-carbaldehyde

Product 1

HCID 35250805-Isopropylthiophene-3-carboxylic acidYield 81.5%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

A solution of AgNO3 (1.01 g, 5.92 mmol)in 10 mL of H20 and 15 mL of a solution of KOH (1.63 g, 40.8 mmol) were sequentially added to a solution of 760 mg (4.9 mmol) of 2-isopropyl-4-thiophene carboxaldehyde, from step 34a above, in 25 mL of ethanol. The resulting black mixture was stirred at room temperature for 2 hours and filtered. The filtrate was washed with ether, then acidified with 6N HCl and extracted with ether. The extract was washed with H2O and brine, dried over MgSO4 and concentrated to give 680 mg (81%) of the title compound as a yellow solid. mp. 64°-67° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with ether
  3. extractionextracted with ether
  4. washThe extract was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-75bd90474137437a97d4623b7899fa0a
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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