One-pot synthesis of 2-hydroxymethyl-5-methylpyrazine from renewable 1,3-dihydroxyacetone

One-pot synthesis of 2-hydroxymethyl-5-methylpyrazine from renewable 1,3-dihydroxyacetone

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00578D, Communication

Lei Song, Mingyuan Zheng, Jifeng Pang, Joby Sebastian, Wentao Wang, Minjie Qu, Jian Zhao, Xinhong Wang, Tao Zhang
An efficient and environmentally benign method for the synthesis of 2-hydroxymethyl-5-methylpyrazine (HMMP) from biomass derived 1,3-dihydroxyacetone was developed.

From the journal:

Green Chemistry

One-pot synthesis of 2-hydroxymethyl-5-methylpyrazine from renewable 1,3-dihydroxyacetone

Lei Song,ab  Mingyuan Zheng,*b  Jifeng Pang,b  Joby Sebastian,b  Wentao Wang,b  Minjie Qu,*a  Jian Zhao,a  Xinhong Wanga  and  Tao Zhangb 

*Corresponding authors

aMaterials Science and Engineering, Dalian Polytechnic University, Dalian, China
E-mail:qumj@dlpu.edu.cn

bState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China
E-mail:myzheng@dicp.ac.cn

Abstract

An efficient and green method for the synthesis of 2-hydroxymethyl-5-methylpyrazine was achieved from biomass derived 1,3-dihydroxyacetone and diammonium phosphate via a one-pot reaction. The product yield was as high as 72% under optimized conditions of pH = 8.0–9.1 at 90 °C for 1 hour in a dioxane and water mixture as a solvent. A possible reaction mechanism was proposed according to the reaction kinetics, NMR and in situ ATR-IR characterization studies.

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC00578D?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

1HNMR (500 MHz, D2O) δ 8.51 – 8.32 (m, 1H), 4.71 (dd, J = 31.0, 6.2 Hz, 1H), 2.49 (d, J = 24.6 Hz, 2H). 13CNMR (126 MHz, D2O) δ 152.99, 151.49, 143.62, 141.27, 61.87, 19.82.

Materials Science and Engineering, Dalian Polytechnic University, Dalian, China

State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China

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http://www.crc.dicp.ac.cn/members1.php?id=557

Dr. Shengmei Lu
Associate Professor
State Key Laboratory of Catalysis
Dalian Institute of Chemical Physics
Chinese Academy of Sciences
457 Zhongshan Road Dalian 116023
Tel: 86-411-84379771
Fax: 86-411-84694447

Sheng-Mei Lu, was born in 1977 in Henan Province. She received her B.S. in 1999 and M. S. degrees in 2002 in chemistry at Central China Normal University in Wuhan. In September 2002, she came to Dalian Institute of Chemical Physics, Chinese Academy of Sciences and received her Ph.D. degree in January 2006. From November, 2006 to December, 2008, she worked as post-doctor in Prof. Carsten Bolm’s group in RWTH-Aachen University with the Alexander Humboldt-Foundation Fellowship. From October 2009, she joined in Prof. Can Li’s group, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences.

Dr. R. Rajesh
State Key Laboratory of Catalysis
Dalian Institute of Chemical Physics
Chinese Academy of Sciences
457 Zhongshan Road, Dalian, 116023, China
Email: rajesh@dicp.ac.cn
Tel: +86-15542638326
Fax : +86-411-84694447

Education

2015, Doctoral Degree, Pondicherry Central University;
2008, Master Degree, Madurai Kamaraj University (Madurai);
2006, Bachelor Degree, Periyar Arts and Science college (Cuddalore);
Working Experience2015.8-present, Post Doctor Fellow, Dalian Institute of Chemical Physics.