Sodium Hydroxide → 9-benzenesulfonyl-9H-carbazol-4-ol

HRID 1836714Notes

Reaction equation

HRID 1836714 reaction equation
[C:1]1([S:7]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([O:23]C(=O)C)[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([S:7]([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11257063HCID 11257063, compound

Product 1

HCID 113478699-benzenesulfonyl-9H-carbazol-4-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 0.96 g of acetic acid 9-benzenesulfonyl-9H-carbazol-4-yl ester (2.62 mmol) in 15 ml of methanol was treated with 3.5 ml of 4 M sodium hydroxide (14 mmol) and stirred at 50° C. for 1.5 h. After cooling to room temperature, methanol was removed from the reaction mixture by rotary evaporation and the residue was partitioned between t-butyl methyl ether and 2N aq. HCl. After drying (Na2SO4) the organic phase was evaporated to dryness to afford 0.84 g (99%) of 9-benzenesulfonyl-9H-carbazol-4-ol as an orange brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. custommethanol was removed from the reaction mixture by rotary evaporation
  3. customthe residue was partitioned between t-butyl methyl ether and 2N aq. HCl
  4. dry with materialAfter drying (Na2SO4) the organic phase
  5. customwas evaporated to dryness

Sources & evidence

ORD record
ord-32ab6bd3d44a44e2a5299a7d2587e21e
Source dataset
uspto-grants-2004_08
Patent number
US06777559B2

Reaction notes

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