Hydrochloric Acid → 2-Methyl-11-phenyl-11-amino-undeca-4,8-dienal oxime
Reaction equation
[CH3:1][CH:2]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=[CH:3]1.Cl.Cl.[NH2:22][OH:23].[OH-].[Na+]>>[CH3:1][CH:2]([CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:4])[CH:3]=[N:22][OH:23]Participants
Procedure
502 g (1.98 mols) of 3-methyl-12-phenyl-1-aza-1,5,9-cyclododecatriene are added dropwise in the course of 1.5 hours to 220 g of 37% hydrochloric acid at a rate such that the temperature does not rise above 80° C. The mixture is then cooled to room temperature (20°-25° C.) and 140 g (2.02 mols) of hydroxylamine hydrochloride are added. About 185 g (4.6 mols) of solid sodium hydroxide are added in the course of one hour, the mixture being cooled with a waterbath, until the pH of the aqueous solution is 10-11. The organic phase which separates out is separated off and washed with water until neutral. 567 g (1.98 mols) of 2-methyl-11-phenyl-11-amino-undeca-4,8-dienal oxime are obtained in the form of a highly viscous liquid; yield 100% of theory.
Workup
- customdoes not rise above 80° C
- additionare added
- temperaturethe mixture being cooled with a waterbath, until the pH of the aqueous solution
- customThe organic phase which separates out is separated off
- washwashed with water until neutral
Sources & evidence
- ORD record
- ord-1ee3bbe2c07249e6b1d3e4186b1ca6e7
- Source dataset
- uspto-grants-1982_10
- Patent number
- US04355177
Reaction notes
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