A Simple Synthetic Route for the Preparation of Tetramethylglycolide from Lactic Acid

Poly(tetramethylglycolide), a chemical recyclable polymer, is currently attracting a lot of interest as a substitute for poly(L-lactic acid). We report here a simple and convenient route for the synthesis of tetramethylglycolide (TMG) from lactic acid. This method involves three steps: (1) one-step...

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Bibliographic Details
Published in:Chemistry letters 2013-02, Vol.42 (2), p.159-161
Main Authors: Watanabe, Kohtaro, Andou, Yoshito, Shirai, Yoshihito, Nishida, Haruo
Format: Article
Language:English
Subjects:
Acetone
Hydrolysis
Lactic acid
Synthesis
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Summary:Poly(tetramethylglycolide), a chemical recyclable polymer, is currently attracting a lot of interest as a substitute for poly(L-lactic acid). We report here a simple and convenient route for the synthesis of tetramethylglycolide (TMG) from lactic acid. This method involves three steps: (1) one-step protection of lactic acid by cyclic acetalization employing acetone; (2) α-methylation of the obtained 2,2,5-trimethyl-1,3-dioxolan-4-one; and (3) one-pot synthesis of TMG including the hydrolysis of 2,2,5,5-tetramethyl-1,3-dioxolan-4-one. We found significant advantages of the incorporation of existing reactions in the synthesis of TMG.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2013.159