(Z)-2-diazonio-1-(4-methylphenyl)ethenolate synthesis

8synthesis methods

Product Name:(Z)-2-diazonio-1-(4-methylphenyl)ethenolate
CAS Number:17263-64-8
Molecular formula:C9H8N2O
Molecular Weight:0

16208-14-3
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(Z)-2-diazonio-1-(4-methylphenyl)ethenolate

17263-64-8
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Yield:17263-64-8 96%

Reaction Conditions:

with caesium carbonate;toluene-4-sulfonic acid hydrazide in chloroform at 20; for 0.0833333 h;

Steps:

4.2. General procedure for synthesis of 3 (3a as an example)

General procedure: 4.2. General procedure for synthesis of 3 (3a as an example) A reaction mixture of phenylglyoxal monohydrate 1a (152.2 mg,1.0 mmol), tosylhydrazine 2 (186.2 mg, 1.0 mmol), and Cs2CO3(977.4 mg, 3.0 mmol) in CHCl3 (2 mL) was stirred at room tem-perature for 5 min. Water (50 mL) was then added to the mixture.The organic layer was separated and the aqueous layer wasextracted with EtOAc (50 mL3). The product was dried over an-hydrous Na2SO4 and concentrated under reduced pressure. Theresidue was puried by column chromatography on silica gel (pe-troleum ether/EtOAc5/1) to afford the desired product 3a.

References:

Shu, Wen-Ming;Ma, Jun-Rui;Zheng, Kai-Lu;Sun, Hui-Ying;Wang, Mei;Yang, Yan;Wu, An-Xin [Tetrahedron,2015,vol. 70,# 49,p. 9321 - 9329]

874-60-2 Synthesis