Benzenesulfonyl chloride → HCID 9862505, compound

HRID 1282446Notes

Reaction equation

HRID 1282446 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:4]=2[CH:3]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.[OH-].[Na+].O>[C:14]1([S:20]([O:1][C:2]2[CH:13]=[CH:12][C:5]3[S:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:4]=3[CH:3]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 114128975-Hydroxybenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 9862505HCID 9862505, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

5-Hydroxybenzo[b]thiophene-3-carboxylic acid (11) (M.Martin-Smith et al. J. Chem. Soc (C), 1899-1905 (1967) 8.63 g (44.4 mmol)) was dissolved in aqueous tetrahydrofuran (water content, 20%; 160 ml) and 1 N sodium hydroxide (44 ml). To the solution were added dropwise 0.56 N sodium hydroxide (87 ml) and benzenesulfonyl chloride (6.2 ml, 48.4 mmol) simultaneously with stirring under ice-cooling while maintaining the pH at 11-12. After the completion of the reaction, the mixture was diluted with water, basified, and washed with toluene. The aqueous layer was made slightly acidic by adding concentrated hydrochloric acid with stirring, and the deposited crystals were filtered, washed with water and dried to provide 14.33 g of 5-benzenesulfonyloxybenzo[b]thiophene-3-carboxylic acid (12). M.p. 202-203° C.

Workup

  1. temperaturecooling
  2. temperaturewhile maintaining the pH at 11-12
  3. customAfter the completion of the reaction
  4. washwashed with toluene
  5. additionby adding concentrated hydrochloric acid
  6. stirringwith stirring
  7. filtrationthe deposited crystals were filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-2a8e64f9fd524b988f0d710249f63955
Source dataset
uspto-grants-2002_09
Patent number
US06455741B1

Reaction notes

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