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ChemicalBook CAS DataBase List 3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol synthesis

11synthesis methods
3-Dimethylaminophenol is used to synthesize dyes and pharmaceutical intermediates. The traditional production process of this compound is to react m-aminophenol with dimethyl sulfate and then purify it in multiple steps to obtain 3-(N, N-dimethylamino)phenol. The production process requires highly toxic dimethyl sulfate, which has high requirements for safe production and raw material transportation and is not conducive to industrial production. Another method is to first react resorcinol with dimethylamine aqueous solution to obtain 3-(N, N-dimethylamino)phenol crude product, then add industrial liquid alkali to the crude product, and then add toluene to extract by-products. After neutralising the aqueous phase, wash to remove the unreacted resorcinol and then distil under reduced pressure to obtain 3-(N, N-dimethylamino)phenol. The operation is simple, the product purity is high, the raw materials are easy to store and transport, and it is easy to industrialize and produce safely.
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Yield:99-07-0 93%

Reaction Conditions:

with hydrogen in water at 200; under 375.038 Torr; for 3 h;Autoclave;Reagent/catalyst;

Steps:

2. Experimental section
General procedure: General procedure for the amination of resorcinol with secondaryamine catalyzed by Raney Ni. Resorcinol (2.2 g, 20 mmol), secondaryamine (30 mmol) and Raney Ni (110 mg) were added to water(50 ml) in a 100 ml autoclave. The autoclave was purged with hydrogengas three times, then maintained 0.05 Mpa pressure. The mixturewas heated to 200 °C rapidly. Then stirring was maintained for 3 h.The reaction mixture was cooled to room temperature, and then extractedwith N-butyl acetate. The organic layer was dried (MgSO4), filteredand concentrated to give the crude product. The pure productwas got through flash column chromatography on silica gel (petroleumether/acetylacetic ester (3/1, v/v)).

References:

Ge, Xin;Pan, Jiong-Bin;Qian, Chao;Feng, Lie;Chen, Yun-Bin;Chen, Xin-Zhi [Catalysis Communications,2014,vol. 46,p. 201 - 207]

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