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ChemicalBook CAS DataBase List 4-Amino-2,3-dichlorphenol
39183-17-0

4-Amino-2,3-dichlorphenol synthesis

4synthesis methods
-

Yield:39183-17-0 83%

Reaction Conditions:

with hydrogenchloride;sodium hydroxide;hydrogen;aniline;sodium nitrite;aluminum nickel in methanol;water

Steps:

6 EXAMPLE 6
EXAMPLE 6 At 0 to 5° C., a solution of 3.8 g (0.055 mol) of NaNO2 in 6 ml of H2 O is added dropwise to 25 ml of aqueous HCl (15%) and 4.9 g (0.0525 mol) of aniline in a 100 ml two-neck flask fitted with internal thermometer and magnetic stirrer. After 10 minutes, this diazonium salt solution is added at 5 to 10° C. to a solution of 8.15 g (0.05 mol) of 2,3-dichlorophenol and 10 g (0.25 mol) of NaOH in 100 ml of H2 O. The mixture is allowed to warm to room temperature, stirred for a further 1 hour and neutralized with aqueous HCl (pH=7). In a 500 ml three-neck flask fitted with internal thermometer, stirrer and gas inlet tube, this solution is admixed with 300 ml of methanol, 2.5 g of Raney nickel and 15 μl of bis(2-hydroxyethyl) sulphide, and the flask is flushed with argon. At 40 to 50° C., 2300 ml of hydrogen (0.1 mol) are then applied with a pressure of about 1 bar over 1.5 hours. The reaction mixture is admixed with a little activated charcoal, stirred for a further 15 minutes and filtered over a bed of silica gel. The methanol is distilled off and pure 4-hydroxy-2,3-dichloroaniline precipitates from the aqueous solution, giving a yield of 83%.

References:

Bayer Aktiengesellschaft US6124504, 2000, A

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