The Journal of Organic Chemistry

Sequential acetalization-pyrolysis of. alpha.-acetylcinnamates and. alpha.-acetylbenzalacetones. A method for the generation of 2-carbonyl-substituted naphthalenes

JR Zoeller, CE Sumner

Index: Zoeller, Joseph R.; Sumner, Charles E. Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 319 - 324

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Citation Number: 22

Abstract

Substituted 2-acetonaphthones and 2-naphthoate methyl esters can be generated from benzaldehydes in a sequence of three reaction steps. Knoevenagel condensation of a benzaldehyde with 2, 4-pentanedione or methyl acetoacetate yields a-carbonyl-substituted benzalacetones. The a-carbonyl-substituted benzalacetones are then cyclized to generate the a-carbonyl-substituted naphthalenes by a sequential acetalization with trimethyl or- ...