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ChemicalBook CAS DataBase List 4-(DIMETHYLAMINO)SALICYLALDEHYDE
41602-56-6

4-(DIMETHYLAMINO)SALICYLALDEHYDE synthesis

6synthesis methods
N,N-Dimethylformamide

68-12-2

3-Dimethylaminophenol

99-07-0

4-(DIMETHYLAMINO)SALICYLALDEHYDE

41602-56-6

General procedure for the synthesis of 4-(dimethylamino)o-hydroxybenzaldehyde from N,N-dimethylformamide and 3-hydroxy-N,N-dimethylaniline: 13.8 g (0.1 mol) of a mixture of 3-hydroxy-N,N-dimethylaniline and 16.0 g (0.22 mol) of N,N-dimethylformamide was slowly added dropwise at 20-40 °C, followed by the addition of methylsulfonyl chloride (0.125 mol), and the rate of titration was controlled to keep the reaction temperature from exceeding 40 °C. After the titration was completed, the reaction was stopped and the reaction temperature was reduced. After the dropwise addition, the reaction mixture was stirred at 50 to 100 °C for 1.0 hour. After completion of the reaction, the reaction solution was cooled to 30 °C and hydrolyzed by adding an appropriate amount of water. After filtration and washing with a small amount of water, 15.0 g of 4-N,N-dimethyl-2-hydroxybenzaldehyde was obtained with a yield of 90.9% and a purity of 95.5%.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1: chlorobenzene / 6 h / 100 °C / Inert atmosphere
2: hydrogenchloride; water / 2 h / 25 °C

References:

Hocker, Jürgen;Giesecke, Henning [Organic Syntheses,1981,vol. 60,p. 49 - 49]

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