Methyl 1-benzofuran-5-carboxylate → 1-Benzofuran-5-Carboxylic Acid

HRID 2181646Notes

Reaction equation

HRID 2181646 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12]C)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1>CO.[OH-].[Na+]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 12674941Methyl 1-benzofuran-5-carboxylate

Product 1

HCID 5956561-Benzofuran-5-Carboxylic AcidYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of methyl benzofuran-5-carboxylate (1.3 g, 7.38 mmol) in MeOH (51 mL) and sodium hydroxide (41 mL of a 5% aqueous solution) is heated to 65° C. for 4 h. The mixture is cooled to rt, and MeOH is removed in vacuo. The remaining aqueous layer is extracted with CH2Cl2. The CH2Cl2 layer is discarded, and the aqueous layer is acidified to pH=1 with concentrated hydrochloric acid. The aqueous layer is extracted with CHCl3. The organic layer is washed with water, dried (MgSO4), filtered and concentrated in vacuo to afford 1.2 g (98%) of benzofuran-5-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.9, 8.30, 8.11, 7.92, 7.69, 7.09.

Workup

  1. temperatureThe mixture is cooled to rt
  2. customMeOH is removed in vacuo
  3. extractionThe remaining aqueous layer is extracted with CH2Cl2
  4. extractionThe aqueous layer is extracted with CHCl3
  5. washThe organic layer is washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3d97d2bfe95416cb6771756392a4b84
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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