Preparation of benzyl cyanides
AssigneeShell Oil Company
InventorsPieter A. Verbrugge, Elisabeth W. Uurbanus
Life of this patent
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Abstract
Optionally ring-substituted benzyl cyanides are prepared by reacting the corresponding benzyl halide with an aqueous phase containing cyanide ions in the presence of a liquid organic phase containing (a) the benzyl halide, (b) a salt which dissociates in water to form cyanide ions, and (c) an onium salt or hydroxide, which reaction is conducted in the absence of water or using an amount of water to benzyl halide below about 0.1. The resulting cyanides can be alkylated at the alpha position using a sec-alkyl halide.
Claims15
A process for the preparation of compounds of the formula ##STR4## wherein R.sup.1 represents a secondary alkyl group having from 3 to 6 carbon atoms;
- and Y represents a hydrogen atom or a halogen atom of atomic number from 9-35, inclusive, which process comprises contacting an organic phase containing a compound of the formula ##STR5## and a sec-alkyl halide of the formula
- Hal -- R.sup.1 IV
- in which formulas II and IV R.sup.1 and Y have the meanings stated above and Hal represents a halogen atom having an atomic number from 17 to 53, inclusive, with an aqueous phase containing an alkali metal hydroxide or with a solid alkali metal hydroxide in the presence of a tetrahydrocarbylammonium halide, using a molar ratio of sec-alkyl halide of formula IV to compound of formula II of at least 3.
A process for the preparation of substituted benzyl nitrile derviatives which comprises (a) reacting a benzyl halide of the formula ##STR6## wherein Y represents a hydrogen atom or a halogen atom of atomic number from 9 to 35, inclusive, and X represents a halogen atom of atomic number 17 to 53, inclusive, with sodium cyanide, which reaction is performed in the presence of a liquid organic phase containing the benzyl halide, sodium cyanide and a tetrahydrocarbylammonium halide, either in the absence of water or using a volume ratio of water to benzyl halide of below 0.1 and (b) reacting the resulting organic phase containing a benzyl nitrile with a sec-alkyl halide of the formula Hal--R.sup.1 wherein R.sup.1 represents a secondary alkyl group having from 3 to 6 carbon atoms and Hal represents a halogen atom having an atomic number of from 17 to 53, inclusive, with an aqueous phase containing an alkali metal hydroxide or with a solid alkali metal hydroxide also in the presence of the tetrahydrocarbylammonium halide and using a molar ratio of sec-alkyl halide reactant to benzyl nitrile reactant of at least 3.
Dependencies are inferred from the claim text.