ChemicalBook CAS DataBase List 1,4-Bis(4-aminophenoxy)benzene

1,4-Bis(4-aminophenoxy)benzene synthesis

5synthesis methods

Product Name:1,4-Bis(4-aminophenoxy)benzene
CAS Number:3491-12-1
Molecular formula:C18H16N2O2
Molecular Weight:292.33

20638-32-8

3491-12-1

GENERAL METHODS: A mixture of compounds 1b, 2b or 3b (1.8 g, 5.1 mmol) with 10% Pd/C (0.2 g) in methanol (70 mL) was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was treated by diafiltration, followed by addition of water (50 mL) to the filtrate and extraction with dichloromethane three times (50 mL each). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and subsequently concentrated under vacuum. The crude product was purified by column chromatography to afford the target products 1c-3c as brown solids in 56.0%, 55.0% and 69.0% yields, respectively.

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3491-12-1
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Yield:3491-12-1 69%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20;Inert atmosphere;Schlenk technique;

Steps:

2.2.1.1 Synthesis of 1c-3c

General procedure: The mixture of compound 1b, 2b or 3b (1.8g, 5.1mmol) and Pd/C (10%, 0.2g) was stirred in methanol (70mL) for overnight under an hydrogen atmosphere at room temperature. After completion of present reaction, the mixture was processed by suction filtration, and then added 50mL water to the resulting filtrate, extracted with dichloromethane three times (3×50mL). The combined organic layers were washed with brine, dried (Na₂SO₄), and concentrated in vacuo. The crude product was purified by column chromatography, affording the expected brown solid products 1c-3c in a yield of 56.0%, 55.0% and 69.0% respectively.

References:

Chen, Zhao;Li, Zheng;Yang, Lan;Liang, Jinhua;Yin, Jun;Yu, Guang-Ao;Liu, Sheng Hua [Dyes and Pigments,2015,vol. 121,p. 170 - 177]

123-31-9 Synthesis