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ChemicalBook CAS DataBase List 4-(2-METHOXYETHOXY)ANILINE
33311-29-4

4-(2-METHOXYETHOXY)ANILINE synthesis

7synthesis methods
4-NITROPHENYL-2-METHOXYETHYL ETHER

22483-40-5

4-(2-METHOXYETHOXY)ANILINE

33311-29-4

General procedure for the synthesis of 4-(2-methoxyethoxy)aniline from 4-nitrophenyl-2-methoxyethyl ether: 1-(2-methoxyethoxy)-4-nitrobenzene (38) (3.9 g, 20 mmol), methanol (80 mL), and 10% activated carbon (400 mg) were added to a hydrogenation reactor. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the activated carbon. The filtrate was concentrated in vacuum to afford 4-(2-methoxyethoxy)aniline (39) (3.1 g, 93% yield) as a black oily product. m/z (M+1) 168.1 was shown by LC-MS (ESI) analysis.

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Yield: 76.9%

Reaction Conditions:

with dimethyl sulfoxide;potassium hydroxide at 60;

Steps:

7 Synthesis of intermediate 4- (2-methoxyethoxy) aniline
P-fluoronitrobenzene (0.5g, 3.54mmol),Ethylene glycol methyl ether (0.335ml, 4.25mmol), potassium hydroxide (0.3g, 5.31mmol) was added to 10ml of dimethyl sulfoxide, stirred at 60 overnight, water analysis, suction filtration0.537 g of a yellow solid was obtained with a yield of 76.9%.

References:

China Pharmaceutical University;Xiang Hua;Teng Yu;Li Zhenbang;Xiao Maoxu;Ren Shengnan;Ha Si;Tong Chao CN111057021, 2020, A Location in patent:Paragraph 0088-0090

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