Benzenesulfonyl chloride → HCID 9862505, compound

HRID 1634311Notes

Reaction equation

HRID 1634311 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

To a solution of 8.63 g (44.4 mmol) of 5-hydroxybenzo[b]thiophene-3-carboxylic acid (1) (J. Chem. Soc (C), 1899-1905 (1967), M. Martin-Smith et al.) in 160 ml of 80% aqueous tetrahydrofuran and 44 ml of 1N sodium hydroxide were added dropwised 87 ml of 0.56N sodium hydroxide and 6.2 ml (48.4 mmol) of benzenesulfonylchloride simultaneously with keeping at pH 11-12 and stirring under ice-cooling. After the reaction, the mixture was diluted with water, alkalized and washed with toluene. The aqueous layer was weakly acidified with conc. hydrochloric acid under stirring. The precipitated crystals were filtered, washed with water and dried to give 14.33 g of 5-benzenesulfonyloxybenzo[b]thiophene-3-carboxylic acid (2).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. washwashed with toluene
  4. stirringunder stirring
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5ec668eb078f4e47866e8dd2b5651eec
Source dataset
uspto-grants-2003_01
Patent number
US06506789B2

Reaction notes

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