3-Chlorobenzoic Acid → HCID 20437619, compound
Reaction equation
O=O.O.O.O.O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][O-:14])=[O:12].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](=[O:25])[O:23][O-].[Mg+2:29].C1(C)C=CC(S(O)(=O)=[O:37])=CC=1.[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45]([OH:47])=[O:46].[Cl:51][C:52]1[CH:53]=[C:54]([CH:59]=[CH:60][CH:61]=1)[C:55]([O:57][OH:58])=[O:56]>>[OH2:12].[OH2:23].[OH2:37].[OH2:46].[Cl:51][C:52]1[CH:53]=[C:54]([CH:59]=[CH:60][CH:61]=1)[C:55]([O:57][O-:58])=[O:56].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](=[O:12])[O:13][O-:14].[Mg+2:29].[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O-:25])=[O:23].[Cl:41][C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45]([O-:47])=[O:46].[Mg+2:29]Participants
7
Procedure
These data are consistent with our assignment of the product from Example 1 as magnesium bis(3-chloroperoxybenzoate) tetrahydrate. A reanalysis of this product in deuterated methanol again showed signals at 174.49 and 172.65 ppm. Addition of 4-toluenesulfonic acid to protonate this product resulted in a shift of the signals to 168.05 and 165.88 ppm, features consistent with 3-chlorobenzoic acid and 3-chloroperoxybenzoic acid formed from protonation of magnesium bis(3-chloroperoxybenzoate) tetrahydrate [and the corresponding decomposition product, magnesium bis (3-chlorobenzoate)]. The results show that the product from Example 1 is the same after protonation in solution as the corresponding peroxycarboxylic acid.
Workup
- customresulted in a shift of the signals to 168.05 and 165.88 ppm
Sources & evidence
- ORD record
- ord-fa55ad41e3fb4d9188366d851a9d9d8d
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04483781
Reaction notes
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