Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2003-04-03
2004-07-13
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S355000, C568S361000, C568S446000, C562S887000, C549S302000, C549S305000, C549S307000
Reexamination Certificate
active
06762327
ABSTRACT:
BACKGROUND OF THE INVENTION
Hypervalent iodine (V) compounds are known to be useful oxidizing agents for the conversion of primary and secondary alcohols to their corresponding aldehydes and ketones, e.g. De Munari, S. et al, Journal of Organic Chemistry, 1996, 61, pp. 9272-9279. Dess-Martin periodinane (DMP), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, is often the reagent of choice for the oxidation of primary and secondary alcohols due to mild reaction conditions (room temperature and either slightly acidic or neutral pH) which are especially suitable for substrates which contain sensitive functional groups. However, DMP explodes violently upon heating under confinement (Chemical & Engineering News, Jul. 16, 1990, p. 3). The hazardous explosive properties of DMP make its use on a manufacturing scale prohibitively dangerous.
Therefore, it is an object of this invention to provide a selective and safe oxidation process for the conversion of a primary or secondary alcohol to the corresponding aldehyde or ketone.
It is another object of this invention to provide an oxidation process which affords high product yields.
It is also an object of this invention to provide a composition useful in the process of this invention.
It is a feature of this invention that the oxidizing agent is used in situ, thereby eliminating the need for additional separation or isolation steps.
These and other objects and features of the invention will become more apparent from the detailed description set forth herein below.
SUMMARY OF THE INVENTION
The present invention provides a safe and effective process for the selective oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone which process reacting said alcohol with a solution containing an anhydride of the formula (RCO)
2
O and a trialkanoyl periodinane compound of formula I
wherein R is C
2
-C
4
alkyl. Preferably, R is ethyl or n-propyl.
The present invention also provides a composition useful in the process of the invention, which composition comprises a solution of an anhydride of the formula (RCO)
2
O and a trialkanoyl periodinane compound of formula I dissolved in a suitable solvent, e.g., an aromatic hydrocarbon such as toluene.
REFERENCES:
patent: 3505354 (1970-04-01), Doebel et al.
patent: 4894386 (1990-01-01), Brown et al.
patent: 4988824 (1991-01-01), Maulding et al.
patent: 5420289 (1995-05-01), Musser et al.
Dess et al. A Useful 12-1-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-1-5 Species. □□Journal of the American Chemical Society, 1991, vol. 113, pp. 7277-7287.*
Barrett et al. Dess-Martin Periodinane Oxidation of Alcohols in the Presence of Stabilized Phosphorus Ylides: A Convenient method for the Homologation of Alcohols Via Unstable Aldehydes. □□Journal of Organic Chemistry, 1997, vol. 62, pp. 9376-9378.*
Sergio De Munari, et al., Journal of Organic Chemistry, 61, 1996, pp. 9272-9279.
Robert E. Ireland, et al., Journal of Organic Chemistry, 58, 1993, pp. 2899.
D.B. Dess, et al., Journal of Organic Chemistry, 48, 1983, pp. 4155-4156.
J.B. Plumb, et al., Chemical & Engineering News, Jul. 16, 1990, p. 3.
Chiacchio Ugo
Di Raimondo Paola
Magnano Mariangela
Miraglia Giuseppe
Rescifina Antonio
Kumar Shailendra
Levis John F.
Witherspoon Sikarl A.
Wyeth
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