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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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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description 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.
doi_str_mv 10.1246/cl.2013.159
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source Oxford University Press:Jisc Collections:OUP Read and Publish 2024-2025 (2024 collection) (Reading list)
subjects Acetone
Hydrolysis
Lactic acid
Synthesis
title A Simple Synthetic Route for the Preparation of Tetramethylglycolide from Lactic Acid
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