The Journal of Organic Chemistry

Synthesis of olefins via reduction-decyanation of. beta.,. gamma.-unsaturated nitriles

JA Marshall, R Bierenbaum

Index: Marshall,J.A.; Bierenbaum,R. Journal of Organic Chemistry, 1977 , vol. 42, # 20 p. 3309 - 3311

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Citation Number: 17

Abstract

Scheme I summarizes the synthesis of the title compound 5. Two convenient starting materials, 3-ethylphenol (1) and 3-methoxyacetophenone, are readily available. Phase- transfer-catalyzed methylation of 1 provided quantitatively 3-methoxyethylbenzene (2). Similar high yields of 2 are obtained by Clemmenson reduction of the acetophenone. Attempts to obtain 2 from 3-methoxybenzaldehyde via Wittig reaction with ...