The Journal of Organic Chemistry

General method for the synthesis of phthalaldehydic acids and phthalides from O-bromobenzaldehydes via ortho-lithiated aminoalkoxides

AK Sinhababu, RT Borchardt

Index: Sinhababu, Achintya K.; Borchardt, Ronald T. Journal of Organic Chemistry, 1983 , vol. 48, # 14 p. 2356 - 2360

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Citation Number: 54

Abstract

A general method for the synthesis of phthalaldehydic acids and phthalides, many of which me key intermediates in natural product synthesis, has been developed. o- Bromobenzaldehydes la-f were first protected in situ as a-morpholinoalkoxides by reaction with lithium morpholide. Treatment of the a-morpholinoalkoxides 3a-f with n-butyllithium (to exchange bromine with lithium) followed by sequential treatment with solid COz and dilute ...

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