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Synthesis 2003(6): 0863-0870
DOI: 10.1055/s-2003-38693
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Base-Induced Alcoholysis of N-Arylmaleimides: Facile in situ Oxa-Michael Addition to Alkyl Maleanilates: Two-Step One-Pot Rapid Access to Alkoxysuccinic Acids [1]

Santosh B. Mhaske, Narshinha P. Argade*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)5893153; e-Mail: argade@dalton.ncl.res.in;
Further Information

Publication History

Received 27 January 2003
Publication Date:
16 April 2003 (online)

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Abstract

A simple, efficient and general two-step, one-pot approach to alkoxysuccinic acids is described. The potassium carbonate-catalyzed reactions of alcohols with N-p-tolylmaleimide (4) followed by an acid-induced hydrolysis of intermediate products furnished alkoxysuccinic acids 1a-f in 90-98% yields. All the intermediates from the reaction of imide 4 with alcohols have been isolated and characterized, proving that the in situ formed alkyl maleanilates 3 are the actual Michael acceptors.

Key words

N-arylmaleimides - alkyl maleanilates - oxa-Michael addition - alkoxysuccinic acids

1

NCL Communication No. 6630.

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1

NCL Communication No. 6630.

23

The (±)-methoxysuccinic acid(1a) has also been obtained in small amounts by chemical degradation of α-methylvanillyl alcohol [24a] and methylated sugars. [24b]