Sodium Hydroxide → Crystal Violet lactone

HRID 1741271Notes

Reaction equation

HRID 1741271 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[CH:30]=[CH:29][C:6]([CH:7]([C:17]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])[C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>O>[CH3:16][N:14]([CH3:15])[C:11]1[CH:10]=[CH:9][C:8]([C:7]2([C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:31])=[CH:30][CH:29]=3)[C:17]3[C:18](=[CH:22][C:23]([N:26]([CH3:28])[CH3:27])=[CH:24][CH:25]=3)[C:19](=[O:21])[O:20]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1020632-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

Product 1

HCID 73773Crystal Violet lactoneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 ml autoclave, 17.1 g of 2-[4,4'-bis(dimethylamino) benzhydryl]-5-dimethylaminobenzoic acid was charged and dispersed by adding 150 g of water. To the dispersion obtained, 3.4 g of activated carbon; SHIRASAGI-C and 1.63 g of a 49% aqueous NaOH solution were added and reacted at 100° C. for 3 hours under increased air pressure of 15 kg/cm2. After finishing the reaction, the reaction mass was treated by the same procedures as carried out in Example 1 to obtain 16.1 g of desired 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide. The yield was 95%. Formation of by-product in the reaction was 1.3%. Selectivity of reaction was 98.7%.

Workup

  1. additiondispersed
  2. customTo the dispersion obtained
  3. customreacted at 100° C. for 3 hours
  4. temperatureunder increased air pressure of 15 kg/cm2
  5. customthe reaction
  6. additionthe reaction mass was treated by the same procedures

Sources & evidence

ORD record
ord-ae1bb1f9c5d7431fa0d6af397275f62d
Source dataset
uspto-grants-1999_10
Patent number
US05973168

Reaction notes

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