Primary alkyl esters as mediums for oxidations by phase-transfer

Details Primary alkyl esters as mediums for oxidations by phase-transfer Primary alkyl esters as mediums for oxidations by phase-transfer

1977-03-28

1978-03-14

Brust, Joseph Paul

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465R, 260465B, 2604651, 2604652, 260530R, 260586P, 260599, 260600R, C07C12014, C07C 4754, C07C 4500, C07C 4516

Patent

active

040790754

ABSTRACT:
The process of oxidizing organic compounds by dissolving the organic compound in a water-immiscible, inert organic solvent and contacting same with an aqueous hypohalite ion in the presence of a catalytic amount of a quaternary onium salt is improved by employing a primary alkyl ester as the organic solvent. For example, cyclohexylmethylamine is oxidized under mild conditions to a high yield of cyclohexylnitrile by dissolving the amine in ethyl acetate and contacting same with aqueous hypochlorite and in the presence of a catalytic amount of tetra-n-butylammonium chloride.

REFERENCES:
patent: 2375016 (1945-05-01), Marple et al.
patent: 3940429 (1976-02-01), McConaghy Jr. et al.
patent: 3941827 (1976-03-01), Johnson
patent: 3992432 (1976-11-01), Napier et al.
patent: 3996259 (1976-12-01), Lee et al.
Lee et al., Tetrahedron Letters, 20 (May, 1976), pp. 1641-1644.

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