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ChemicalBook CAS DataBase List 4,4'-Ethylenedianisole
1657-55-2

4,4'-Ethylenedianisole synthesis

12synthesis methods
-

Yield: 81%

Reaction Conditions:

with Dimethyl oxalate;manganese;1,2-bis(diphenylphosphino)ethane nickel(II) chloride;lithium bromide in N,N-dimethyl-formamide at 110; for 16 h;Inert atmosphere;Sealed tube;

Steps:

Synthesis of 2a; Typical Procedure
General procedure: The procedure was conducted in an argon-filled glove box. A reaction tube equipped with a magnetic stir bar was charged with Ni(dppe)Cl2(10.6 mg, 0.02 mmol), Mn (44.0 mg, 0.8 mmol), alcohol 1a (48.8 mg,0.4 mmol), DMO (94.5 mg, 0.8 mmol), LiBr (34.7 mg, 0.4 mmol), and DMF (1.5 mL). The reaction tube was then sealed and removed from the glove box. The reaction mixture was stirred at 110 °C for 16 h. After cooling to r.t., the mixture was diluted with EtOAc (40 mL) and washed with water, brine, dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to afford the desired product 2a.

References:

Pan, Feng-Feng;Guo, Peng;Huang, Xiaochuang;Shu, Xing-Zhong [Synthesis,2021,vol. 53,# 17,p. 3094 - 3100]

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