Oxidation method of primary or secondary alcohol

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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C568S361000, C568S402000, C568S431000, C568S471000

Reexamination Certificate

active

11290474

ABSTRACT:
A method for preparing an aldehyde or ketone by oxidizing a primary or secondary alcohol in the presence of a nitroxyl radical compound and a co-oxidant in an organic solvent, which process is characterized in using an organic N-bromoamide compound or a combination of N-chlorosuccinimide and a compound having bromide ion as the co-oxidant.

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patent: 6540876 (2003-04-01), Cimecioglu et al.
patent: 2005/0240050 (2005-10-01), Minamida et al.
patent: 2005/082825 (2005-09-01), None
Einhorn, J. et al., “Efficient and Highly Selective Oxidation of Primary Alcohols to Aldehydes byN-Chlorosuccinimide Mediated by Oxoammonium Salts”,J. Org. Chem., vol. 61, pp. 7452 to 7454 (1996).
Anelli, P. C. et al., “Fast and Selective Oxidation of Primary Alcohols to Aldehydes or to Carboxylic Acids and of Secondary Alcohols to Ketones Mediated by Oxoammonium Salts under Two-Phase Conditions”,J. Org. Chem., vol. 52, pp. 2559 to 2562 (1987).
Miller, Ross et al., “Iodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes and Ketones”,Organic Letters, vol. 5, No. 3, pp. 285 to 287 (2003).
De Luca, Lidia et al., “Trichloroisocyanuric/TEMPO Oxidation of Alcohols under Mild Conditions: A Close Investigation”,J. Org. Chem., vol. 68, No. 12, pp. 4999 to 5001 (2003).
Liu, Renhua et al., “Highly Efficient Catalytic Aerobic Oxidations of Benzylic Alcohols in Water”,J. Org. Chem., vol. 70, No. 2, pp. 729 to 731 (2005).

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