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NAPHTHALENE DERIVATIVES FROM SUBSTITUTED γ-PHENYLCROTONIC ESTERS

 

作者: Léo Marion,   John A. McRae,  

 

期刊: Canadian Journal of Research  (NRC Available online 1940)
卷期: Volume 18b, issue 9  

页码: 265-271

 

ISSN:1923-4287

 

年代: 1940

 

DOI:10.1139/cjr40b-033

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The product of the condensation of phenylacetone with ethyl malonate, i.e., ethyl α-carbethoxy-β-methyl-γ-phenyl-butenoate, when saponified, gives rise to 3-methyl-1-hydroxy-2-naphthoic acid. This can be decarboxylated to a naphthol identical with 3-methyl-1-naphthol prepared by a series of reactions from β-methyl-naphthalene. The synthetic naphthol, in the Kolbe synthesis, yields 3-methyl-1-hydroxy-2-naphthoic acid, identical with the acid produced when the condensation ester is saponified. The condensation of phenylacetone with ethyl cyanoacetate gives rise to an unsaturated ester which does not cyclize spontaneously, but only when heated in glycerol, to a phenolic compound, probably 1-hydroxy-3-methyl-2-naphthoic nitrile.

 

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