Hydrochloric Acid → Benzo(b)thiophene-3-carboxylic acid

HRID 1091316Notes

Reaction equation

HRID 1091316 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[S:9][CH:8]=1)=[O:6].[OH-].[Li+].Cl>O.O1CCCC1>[S: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

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 3939Lithium HydroxideHCID 12514024Methyl 1-benzothiophene-3-carboxylate

Product 1

HCID 601280Benzo(b)thiophene-3-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a methanol (100 mL) solution of 1-benzothiophene-3-carboxylic acid methyl ester (20.6 g, 107 mmol), tetrahydrofuran (200 mL), water (100 mL) and lithium hydroxide (9.00 g, 214 mmol) were added at room temperature, and the mixture was stirred for 15 hours at room temperature. 1N-hydrochloric acid (214 mL, 214 mmol) was added to the reaction liquor, and then methanol was distilled off under reduced pressure. To the obtained aqueous layer, 1N-hydrochloric acid (50 mL, 50 mmol) was added, and the solids generated therefrom were collected by filtration, washed with water, and then dried for two days at 50° C. using a vacuum pump, to obtain the title compound (19.1 g, 100%) as a solid.

Workup

  1. distillationmethanol was distilled off under reduced pressure
  2. filtrationthe solids generated therefrom were collected by filtration
  3. washwashed with water
  4. customdried for two days at 50° C.

Sources & evidence

ORD record
ord-42242d1c9044416d974932378c538b2f
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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