Benzenesulfonyl chloride → HCID 9862505, compound

HRID 2287447Notes

Reaction equation

HRID 2287447 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 88.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 8.63 g (44.4 mol) 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 was added 87 ml of 0.56N sodium hydroxide and 6.2 ml (48.4 mmol) of benzenesulfonylchloride simultaneously with keeping at pH 11-12 with stirring under ice-cooling. After the reaction completion, 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. washwashed with toluene
  3. stirringunder stirring
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c252ccbe6efd4ff490a9ea0fe9ef870c
Source dataset
uspto-grants-2000_07
Patent number
US06083974

Reaction notes

Loading…