Sodium Hydroxide → 6-Methoxy-1-benzothiophene-2-carboxylic acid

HRID 57151Notes

Reaction equation

HRID 57151 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[S:9][C:8]=2[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 534861116-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 204937096-Methoxy-1-benzothiophene-2-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of compound 141-B (6.55 g; 29.4 mmol) in methanol (100 mL) was added 1N NaOH (44.2 mL; 44.2 mmol) and the reaction was heated at 65° C. for 18 h. The reaction was cooled, the solvent evaporated under reduced pressure, the residue dissolved in H2O, cooled to 0° C., acidified with 2N HCl, and the solid filtered, washed with H2O, and dried in vacuo to afford compound 141-C as a white solid (6.01 g, 98%). 1H-NMR (DMSO-d6): δ 3.84 (s, 3H), 7.05-7.08 (m, 1H), 7.60-7.61 (d, 1H), 7.87-7.89 (d, 1H), 8.01 (s, 1H), 13.24 (s, 1H); MS: m/z 208.9 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated under reduced pressure
  3. dissolutionthe residue dissolved in H2O
  4. temperaturecooled to 0° C.
  5. filtrationthe solid filtered
  6. washwashed with H2O
  7. customdried in vacuo

Sources & evidence

ORD record
ord-af97b05cc5ec4c08bedf83d40c786969
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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