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1-Aci-nitro-2-(p-hydroxyphenyl)ethane synthesis

8synthesis methods
3179-08-6 Synthesis
4-HYDROXY-B-NITROSTYRENE

3179-08-6
68 suppliers
$6.00/1g

1-Aci-nitro-2-(p-hydroxyphenyl)ethane

37567-58-1
3 suppliers
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Yield:37567-58-1 96%

Reaction Conditions:

with diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate;S-benzyl isothiouronium chloride in methanol at 60;Inert atmosphere;

Steps:

4.2. Typical procedure for the reduction of conjugated nitroalkenes

General procedure: The mixture of nitroalkenes 1 (0.1 g, 0.67 mmol), Hantzsch ester (0.19 g, 0.74 mmol) and S-benzyl isothiouronium chloride (14 mg, 0.067 mmol) in methanol (5 ml) was stirred at 60 °C for 5-12 h. After completion of the reaction, the crude product in methanol was concentrated and added into the excess cooled CH2Cl2. The S-benzyl isothiouronium chloride was readily precipitated out, and then filtered and washed many times with CH2Cl2 to be reused. The filtrate was evaporated and the residue was purified by flash column chromatography to give the required nitroalkanes products 2. All nitroalkanes except 2j and 2p were characterized with the reported spectroscopic data. [2] and [5]

References:

Nguyen, Quynh Pham Bao;Kim, Jae Nyoung;Kim, Taek Hyeon [Tetrahedron,2012,vol. 68,# 32,p. 6513 - 6516] Location in patent:supporting information; experimental part