Acetic Anhydride → HCID 53674493, compound

HRID 2166760Notes

Reaction equation

HRID 2166760 reaction equation
[Na].[C:2]([O:5][C:6](=[O:8])[CH3:7])(=O)[CH3:3].[C:9]([O-])(=O)C.[K+].[CH:14]1([CH2:20][NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2C(O)CC(OCC)=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(OCC)(=O)C>[CH:14]1([CH2:20][NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH:9]=[CH:7][C:6]([O:5][CH2:2][CH3:3])=[O:8])=[CH:26][CH:27]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 5360545SodiumHCID 20498895HCID 20498895, compound

Product 1

HCID 53674493HCID 53674493, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The 4-(substituted-amino)phenylalkenoic acids may be prepared by condensation of the appropriate aldehydes or by dehydration of the corresponding substituted-phenylhydroxyalkanoic acids. For example, ethyl 5-[4-(cyclopentylmethylamino)phenyl]-2,4-pentadienoate is obtained by the Wittig reaction of 4-(cyclopentylmethylamino)benzaldehyde with the Wittig reagent, triethyl 4-phosphonocrotonate. Alternatively, these alkenoic acids are obtained by heating 4-[N-(10-cyclopentyldecyl-N-methylamino]benzaldehyde and the like 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-[(cyclohexylmethylamino)phenyl]-3-hydroxypropionate to yield ethyl 4-cyclohexylmethylaminocinnamate.

Sources & evidence

ORD record
ord-afa445b76cc249028617a7864a492d50
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

Loading…