Hydrochloric Acid → 5,6-dimethoxy-1-benzothiophene-2-carboxylic acid

HRID 2175701Notes

Reaction equation

HRID 2175701 reaction equation
[CH3:1][O:2][C:3]1[C:15]([O:16][CH3:17])=[CH:14][C:6]2[S:7][C:8]([C:10]([O:12]C)=[O:11])=[CH:9][C:5]=2[CH:4]=1.[OH-].[Na+].Cl>CO.C1COCC1.O>[CH3:1][O:2][C:3]1[C:15]([O:16][CH3:17])=[CH:14][C:6]2[S:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12521858Methyl 5,6-dimethoxy-1-benzothiophene-2-carboxylate

Product 1

HCID 2686205,6-dimethoxy-1-benzothiophene-2-carboxylic acidYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5,6-dimethoxybenzo[b]thiophene-2-carboxylate (1.0 g, 4 mmol) in MeOH (20 mL) and THF (10 mL) was added 2N NaOH (10 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature for 2 hours before adjusting the pH value to 3 with 1 N HCl and diluting with water. The resulting suspension was filtered and the solid was dried under vacuum to afford 5,6-dimethoxybenzo[b]thiophene-2-carboxylic acid as a white solid (890 mg, 94%). LC-MS (ES-API); rt 8.17 min; m/z calculated for C11H10O4S [M+Na]+ 261.0, found 260.9.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-598e5144f65a42d6be83f400c604e868
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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