Reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:22]3[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1.CN(C)C1C=C(C=CC=1)C(O)=O.NC1C=C(C=CC=1)C(O)=O.CI.[OH-].[K+].CN(C)C1C=CC(C(O)C2C=CC(N(C)C)=CC=2)=CC=1.S(=O)(=O)(O)O>>[CH3:30][N:28]([CH3:29])[C:25]1[CH:26]=[CH:27][C:22]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:31])[CH3:1])=[CH:8][CH:7]=2)[C:18]2[CH:17]=[CH:16][C:15]([N:19]([CH3:20])[CH3:21])=[CH:14][C:13]=2[C:11]([OH:12])=[O:10])=[CH:23][CH:24]=1Participants
Reactant 7
Product 1
Procedure
U.S. Pat. No. 2,417,897 and its corresponding U.S. Pat. No. Re. 23,024, which issued Mar. 25, 1947 and Aug. 17, 1948, respectively, disclose a three-step process for the preparation of 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide, Crystal Violet Lactone (CVL). In the first step, 3-dimethylaminobenzoic acid is prepared from 3-aminobenzoic acid by alkylating the free amine using methyl iodide in the presence of potassium hydroxide. In the second step, the 3-dimethylaminobenzoic acid is condensed with 4,4'-bis(dimethylamino)benzhydrol in the presence of sulfuric acid to obtain 2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid. In the third step, the 2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid is oxidized using lead dioxide in dilute hydrochloric acid to obtain the CVL.
Sources & evidence
- ORD record
- ord-511bc6b7428042eca90bc26db83c6f3c
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528136
Linked notes
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