Hydrochloric Acid → Benzoic acid, 4-[1-[[(2,4-dichlorophenyl)amino]carbonyl]-3,3-dimethyl-2-oxobutoxy]-, methyl ester
Reaction equation
Cl.[C:2]([C:5]1[CH:29]=[CH:28][C:8]([O:9][CH:10]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[O:12])=[CH:7][CH:6]=1)([OH:4])=[O:3].[CH3:30]O>>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]([C:22](=[O:27])[C:23]([CH3:24])([CH3:25])[CH3:26])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[O:12])=[CH:28][CH:29]=1)([O:4][CH3:30])=[O:3]Participants
4
Procedure
HCl gas was bubbled into a suspension of N-[2-[4-carboxyphenoxy]-4,4-dimethyl-3-oxopentanoyl]-2,4-dichloroaniline (12.0 g, 28.3 mmol, available from Eastman Kodak, Rochester, N.Y.) in absolute methanol (175 mL) for 30 minutes. The mixture was heated to reflux for 2 hrs during which complete solution was obtained. Upon cooling to room temperature, white crystals of the product began to form. The reaction mixture was cooled in an ice bath, and the solids were collected by filtration, washed with fresh methanol and air-dried to provide N-[2-[4-carbomethoxyphenoxy]-4,4-dimethyl-3-oxopentanoyl]-2,4-dichloroaniline (8.4 g, 68% yield). The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.
Workup
- temperatureThe mixture was heated
- temperatureto reflux for 2 hrs during which complete solution
- customwas obtained
- customto form
- temperatureThe reaction mixture was cooled in an ice bath
- filtrationthe solids were collected by filtration
- washwashed with fresh methanol
- customair-dried
Sources & evidence
- ORD record
- ord-08568d095f774fa8b0a8782ea9c0904f
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05350870
Reaction notes
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