Citation: Xin-Ping Ouyang, Chun-Lei Liu, Yu-Xia Pang, Xue-Qing Qiu. Synthesis of a trimeric lignin model compound composed of α-O-4 and β-O-4 linkages under microwave irradiation[J]. Chinese Chemical Letters, ;2013, 24(12): 1091-1094. shu

Synthesis of a trimeric lignin model compound composed of α-O-4 and β-O-4 linkages under microwave irradiation

1.
School of Chemistry & Chemical Engineering, South China University of Technology, Guangzhou 510640, China

Corresponding author: Xue-Qing Qiu,
Received Date: 9 May 2013
Available Online: 20 July 2013
Fund Project: This work is financially supported by the National Basic Research Program of China (No. 2012CB215302) (No. 2012CB215302) National Natural Science Fundation of China (No. 20876064) (No. 20876064)

A trimeric lignin model compound composed of α-O-4 and β-O-4 linkages was prepared by the microwave-assisted synthesis, which consisted of three steps: (a) the synthesis of 3-methoxy-4- benzyloxyacetophenone (2) from acetovanillone (1), (b) the bromination of compound 2 to produce 3- methoxy-4-benzyloxy-α-bromoacetophenone (3), and (c) followed by a nucleophilic substitution of compound (3) to obtain 3-methoxy-4-benzyloxy-α-(3-methoxy-4-(1-propenyl)phenol)-acetophenone (4). The target product was characterized by MS, ¹H NMR and ¹³C NMR spectroscopy. It was found that the trimeric compound synthesized can be used as a preferable lignin model compound because it contains guaiacyl structural unit (3-methoxy-4-hydroxy phenyl propane) linked by α-O-4 and β-O-4 linkages. In addition, under the conditions of microwave irradiation, the reaction time of each step is significantly reduced, and the selectivity of target product is greatly improved. The yields of each step and the overall sequence are 95.31%, 87.3%, 90.6% and 75.4% (95.31%×87.3%×90.6%), respectively.
- Lignin,
- Microwave irradiation,
- Model compound,
- Synthesis
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沈阳化工大学材料科学与工程学院沈阳 110142