Hydrochloric Acid → 1-Benzofuran-3-carboxylic acid

HRID 1091312Notes

Reaction equation

HRID 1091312 reaction equation
CO.C[O:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH:8]=1)=[O:6].[OH-].[Li+].Cl>O>[O:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([C:5]([OH:6])=[O:4])=[CH:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 3939Lithium HydroxideHCID 127770993-Benzofurancarboxylic acid, methyl ester

Product 1

HCID 5956551-Benzofuran-3-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol (30 mL) solution of 1-benzofuran-3-carboxylic acid methyl ester (5.25 g, 29.8 mmol) tetrahydrofuran (60 mL), water (30 mL) and lithium hydroxide (2.50 g, 59.9 mmol) were added at room temperature. The mixture was stirred for 15 hours at room temperature. 1N-hydrochloric acid (60 mL, 60 mmol) was added to the reaction liquor, and then methanol was distilled off under reduced pressure. 1N-hydrochloric acid (15 mL, 15 mmol) was added to the obtained aqueous layer, and solids generated therefrom were collected by filtration. The solids were washed with water, and then dried for two days at 50° C. with a vacuum pump, to obtain the title compound (4.41 g, 27.2 mmol, 91%) as a solid.

Workup

  1. distillationmethanol was distilled off under reduced pressure
  2. filtrationgenerated therefrom were collected by filtration
  3. washThe solids were washed with water
  4. customdried for two days at 50° C. with a vacuum pump

Sources & evidence

ORD record
ord-33b6684450304ffdb882e99925e27393
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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