Potassium Hydroxide → 3,5-Di(carbazol-9-yl)benzoic acid

HRID 1037514Notes

Reaction equation

HRID 1037514 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([N:24]4[C:36]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[C:30]5[C:25]4=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:23]=3)[C:17]([O:19]C)=[O:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C1COCC1.CO.O>[CH:10]1[C:11]2[N:12]([C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([N:24]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=5[C:31]5[C:36]4=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:23]=3)[C:17]([OH:19])=[O:18])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59638298Methyl 3,5-di(carbazol-9-yl)benzoate

Product 1

HCID 596383053,5-Di(carbazol-9-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3,5-di(carbazol-9-yl)benzoate (1.0 g, 2.14 mmol) in THF/methanol (25.0 ml, 15:10) was added KOH (0.6 g, 10.69 mmol) in water (2.0 ml) at room temperature under stirring. The reaction was carried out at room temperature for 4.5 hours. The THF was evaporated. Next, methanol (20.0 ml) was added and then HCl water solution (80.0 ml; 15.0 ml of 36-38% HCl in 65.0 ml of water) was added. The mixture was stirred for 1 hour and a pale yellow solid product was obtained by filtration. The product was purified by recrystallization from acetone/water: 0.95 g (97.9%).

Workup

  1. customThe THF was evaporated
  2. additionNext, methanol (20.0 ml) was added
  3. additionHCl water solution (80.0 ml; 15.0 ml of 36-38% HCl in 65.0 ml of water) was added
  4. stirringThe mixture was stirred for 1 hour
  5. customa pale yellow solid product was obtained by filtration
  6. customThe product was purified by recrystallization from acetone/water

Sources & evidence

ORD record
ord-92b25e5c03a142ff9bc9b3b93c823ba6
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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