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Journal of Carbohydrate Chemistry Volume 37, 2018 - Issue 2
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Original Articles

Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction

Zekun DingSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Xiaosheng LuoSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Yibin MaSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Heshan ChenSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Saifeng QiuSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Guosheng SunSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Wan ZhangSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Chao YuSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
,
Zhenliang WuSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaView further author information
&
Jianbo ZhangSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai, ChinaCorrespondence[email protected]
View further author information
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Pages 81-93 | Received 21 Nov 2017, Accepted 14 Jan 2018, Published online: 08 Feb 2018
 
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ABSTRACT

5-Hydroxymethylfurfural was conveniently synthesized by dehydration of D-fructose in a good yield. To further build bioactive derivatives from 5-hydroxymethylfurfural, 2,3-unsaturated glycosides were directly obtained through the Ferrier-rearrange-ment reaction of various glycals. Noticeably, a solid acid catalyst was successfully applied in the preparation of 5-hydroxyme-thylfurfural and then recycled to promote the Ferrier-rearrang-ement reaction, making it possible to achieve two steps of reaction in an eco-friendly manner through the simple process.

GRAPHICAL ABSTRACT

Acknowledgments

We sincerely thank the analytic center of East China Normal University for data measurements.We also express our gratitude to Mr. Tianjun Tang for his suggestions of manuscript modification.

Additional information

Funding

The project was supported by the Natural Science Foundation of Shanghai (11ZR1410400), “DAXIA” Science Research Foundation of East China Normal University (2012DX-138), large instruments Open Foundation of East China Normal University (20151043 & 20162015), and National Undergraduate Training Program for Innovation and Entrepreneurship (201710269030G).

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