Sodium Hydroxide → 4-Isopropoxy-1-benzofuran-2-carboxylic acid

HRID 29339Notes

Reaction equation

HRID 29339 reaction equation
[CH:1]([O:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([O-:16])=[O:15])[O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[CH:1]([O:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([OH:16])=[O:15])[O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 865990294-Isopropoxy-1-benzofuran-2-carboxylate

Product 1

HCID 687115444-Isopropoxy-1-benzofuran-2-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.15 g (0.62 mmole) of 4-isopropoxy-1-benzofuran-2-carboxylate in 2.5 mL of methanol and 2.5 mL of THF was added 3 mL of 1N sodium hydroxide solution. The solution was stirred at room temperature for 45 minutes. The reaction mixture was concentrated in vacuo, the residue was diluted with water and neutralized with 1N HCl to pH ˜3-4, and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 0.13 g of 4-isopropoxy-1-benzofuran-2-carboxylic acid. Yield 94%. m.p. 148-150° C. MS: 219.1(M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with water and neutralized with 1N HCl to pH ˜3-4
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bfac87cc9ea4d78a07057e6a22b5d93
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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