Acetic Anhydride → HCID 53674493, compound

Participants

Reaction Steps

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.

Provenance & Evidence