Acetic Anhydride → Ethyl 4-[15-(trifluoromethyl)pentadecylamino]cinnamate
Reaction equation
[Na].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[F:14][C:15]([F:47])([F:46])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38](O)[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:34][CH:33]=1>C(OCC)(=O)C>[F:14][C:15]([F:46])([F:47])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:34][CH:33]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The [4-(polyfluoroalkylamino)phenyl]alkenoic acids may be prepared by condensation of the appropriate aldehydes or by dehydration of the corresponding substituted-phenyl-hydroxyalkanoic acids. For example, ethyl 5-{4-[15-(trifluoromethyl)pentadecylamino]phenyl}-2,4-pentadienoate is obtained by the Wittig reaction of 4-[15-(trifluoromethyl)pentadecylamino]benzaldehyde with the Wittig reagent, triethyl 4-phosphonocrotonate. Alternatively, these alkenoic acids are obtained by heating 4-[N-polyfluoroalkyl-N-(methyl or acetyl)amino]benzaldehydes with the sodium salt of the carbanion of ethyl acetate or with a mixture of ethyl acetate, acetic anhydride and potassium acetate. The second method is illustrated by dehydration of ethyl 3-{4-[15-(trifluoromethyl)pentadecylamino]phenyl}-3-hydroxypropionate to yield ethyl 4-[15-(trifluoromethyl)pentadecylamino]cinnamate.
Sources & evidence
- ORD record
- ord-e224ca30df66489799ef5451d6e8c24e
- Source dataset
- uspto-grants-1980_05
- Patent number
- US04205085
Reaction notes
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