Citation: Cheng-Xi Zhang, Yu-Yuan Deng, Yi-Yang Zhang, Po Yang, Yi Gu. Study on products and reaction paths for synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine from phenol, aniline and formaldehyde[J]. Chinese Chemical Letters, ;2015, 26(3): 348-352. doi: 10.1016/j.cclet.2014.12.005 shu

Study on products and reaction paths for synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine from phenol, aniline and formaldehyde

1.
State Key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Po Yang, Yi Gu,
Received Date: 29 September 2014
Available Online: 19 November 2014
Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21174093). (No. 21174093)

To study the synthesis of 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine (benzoxazine), the reaction paths of phenol, aniline and formaldehyde were investigated by analyzing the synthesis crude products. With the aid of high-performance liquid chromatography (HPLC), chromatographic column and preparative HPLC, seven compounds originated from the crude products were obtained and their chemical structures were elucidated. Possible reaction paths are proposed based on these compounds. Results show that Nhydroxymethyl aniline (HMA) derived from the reaction of formaldehyde and aniline is probably the key intermediate during the reaction. HMA can react with itself or other reactants to form other intermediates, such as 1,3,5-triphenyl-1,3,5-triazinane and 2-((phenylamino)methyl)phenol, and further form benzoxazine and byproducts.
- Benzoxazine,
- Synthesis reaction path,
- Synthetic product,
- Competing reaction,
- Intermediate
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