Hydrochloric Acid → 5-Hydroxybenzo[b]thiophene-3-carboxylic acid

HRID 2299570Notes

Reaction equation

HRID 2299570 reaction equation
C1(S([O:10][C:11]2[CH:22]=[CH:21][C:14]3[S:15][CH:16]=[C:17]([C:18]([OH:20])=[O:19])[C:13]=3[CH:12]=2)(=O)=O)C=CC=CC=1.Cl>[OH-].[Na+]>[OH:10][C:11]1[CH:22]=[CH:21][C:14]2[S:15][CH:16]=[C:17]([C:18]([OH:20])=[O:19])[C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9862505HCID 9862505, compound

Product 1

HCID 114128975-Hydroxybenzo[b]thiophene-3-carboxylic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

5-Benzenesulfonyloxybenzo[b]thiophene-3-carboxylic acid (6) (100 mg, 0.3 mmol) prepared in Examples above was dissolved in 1 N sodium hydroxide (1.2 ml) and heated at 40° C. for 8 hours with stirring. To the reaction solution was added 1 N hydrochloric acid (1.2 ml), and the deposited crystals were filtered, washed with water and dried to provide 58 mg of the title compound (11). Yield: 96.6% mp 262-263° C.

Workup

  1. filtrationthe deposited crystals were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d7cb6a1488e74192b6098aa6002d62ef
Source dataset
uspto-grants-2002_12
Patent number
US06495702B2

Reaction notes

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