Sodium Hydroxide → Crystal Violet lactone

HRID 1741270Notes

Reaction equation

HRID 1741270 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 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

To a 500 ml reaction vessel, 21.5 g of 2-[4,4'-bis(dimethylamino) benzhydryl]-5-dimethylaminobenzoic acid having a purity of 97.0% was charged and 250 g of water was added. To the dispersion thus obtained, 21.5 g of activated carbon; SHIRASAGI-C (manufactured by Takeda Chemical Ind. Co.) and 2.0 g of a 49% aqueous NaOH solution were added and stirred at 90 to 95° C. Through the reaction system thus obtained air was blown for 9 hours at a rate of 400 ml/min. After finishing the reaction, the reaction mass was filtered and the obtained cake was slurried in water, and completely dissolved by adding 19.5 g of a 36% aqueous HCl solution. Thereafter, the activated carbon was filtered. The filtrate was neutralized to pH7.0 with a 49% aqueous NaOH solution. The precipitated crystals were filtered, washed and dried to obtain 20.1 g of 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide. The yield was 95.4%. Formation of by-product in the reaction was 1.5%. Selectivity of reaction was 98.4%.

Workup

  1. additionwas charged
  2. customTo the dispersion thus obtained
  3. customthe reaction
  4. filtrationthe reaction mass was filtered
  5. dissolutioncompletely dissolved
  6. additionby adding 19.5 g of a 36% aqueous HCl solution
  7. filtrationThereafter, the activated carbon was filtered
  8. filtrationThe precipitated crystals were filtered
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-c767b70c7b054504b6fdc28349aa6773
Source dataset
uspto-grants-1999_10
Patent number
US05973168

Reaction notes

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