Hydrogen Peroxide → Crystal Violet lactone

HRID 1679818Notes

Reaction equation

HRID 1679818 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+].OO>>[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 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1020632-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

Product 1

HCID 73773Crystal Violet lactone

Conditions

Temperature
70 °C

Procedure

To 1,500 wt. parts of an aqueous solution containing 41.7 wt. parts of 2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid and 4.4 wt. parts of sodium hydroxide was added 0.4 wt. part of cobaltous chloride. The mixture was heated at 70° C. and 51 wt. parts of 10% aqueous solution of hydrogen peroxide was added dropwise during 1 hour (pH=9.9). The precipitate was separated and dissolved into toluene and the catalyst was separated by a filtration and toluene was distilled off to obtain 39.8 wt. parts of 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide having a melting point of 180° to 183° C.

Workup

  1. customThe precipitate was separated
  2. dissolutiondissolved into toluene
  3. customthe catalyst was separated by a filtration and toluene
  4. distillationwas distilled off

Sources & evidence

ORD record
ord-008a9c35ab4c4d36b78db2b8424a717c
Source dataset
uspto-grants-1981_06
Patent number
US04271075

Reaction notes

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