4-Cyanomethylbenzoic acid synthesis
- Product Name:4-Cyanomethylbenzoic acid
- CAS Number:83901-88-6
- Molecular formula:C11H11NO2
- Molecular Weight:189.21
Yield:83901-88-6 42.2%
Reaction Conditions:
in ethanol;water at 20; for 15 h;Heating / reflux;
Steps:
1.1.c.
1.1.c. Ethyl 4-cyanomethyl-benzoate To a solution of 147.5 g (2.263 mol) of potassium cyanide in 250 ml of hot water is added dropwise a solution of 500 g (2.057 mol) of ethyl 4-bromomethyl-benzoate in 1000 ml of ethanol. The reaction mixture is refluxed for one hour and stirred for 12 hours at ambient temperature. A further 73.7 g (0.5 mol) of potassium cyanide are added and the mixture is refluxed for two hours. The solid in the reaction mixture is filtered off and the filtrate is filtered through a mixture of silica gel and activated charcoal. The filtrate obtained is evaporated down and the residue is poured onto 1000 ml of water. The aqueous solution is extracted with tert-butylmethylether and the organic phase is extracted three times with water. Then the organic phase is dried over magnesium sulphate and the solvent is distilled off using the rotary evaporator. The purification is carried out by column chromatography on silica gel (petroleum ether/ethyl acetate 8:2). Yield: 164.46 g (42.2% of theory); C11H11NO2 (M=189.216); calc.: molar peak (M+H)+: 190 fnd.: molar peak (M+H)+: 190; Rf value: 0.3 (silica gel, petroleum ether/ethyl acetate 8:2).
References:
US2004/242572,2004,A1 Location in patent:Page/Page column 34
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