Production of alkyl aralkyl keones from allylic-aralkenyl second

Details Production of alkyl aralkyl keones from allylic-aralkenyl second Production of alkyl aralkyl keones from allylic-aralkenyl second

1997-02-21

1998-04-21

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 4551

Patent

active

057419388

ABSTRACT:
The process forms an alkyl aralkyl ketone from an aralkenyl secondary alcohol having an allylic double bond relative to the hydroxycarbinyl group, and having the allylic double bond positioned between the aryl moiety and the hydroxycarbinyl group. This is accomplished by heating the alcohol in a chemically indifferent organic liquid medium to which a catalytic quantity of an iron polycarbonyl has been added, so that an internal rearrangement occurs. Among the ketones that can be efficiently produced in this manner is non-steroidal antiinflammatory agent, 4-(6'-methoxy-2'-naphthyl)-butan-2-one, generally known as nabumetone.

REFERENCES:
patent: 4420639 (1983-12-01), Lake et al.
patent: 5101077 (1992-03-01), Drent
patent: 5225603 (1993-07-01), Aslam et al.
Mohammad Aslam et al., "Convenient Syntheses of Nabumetone" Communications, Nov. 1989, pp. 869-870.
Bingham et al., "Homogeneous Catlysis of Olefin Isomerisation. Part VI. Pent-1-ene Isomerisation catalysed by Solutions of Dodecacarbonyltri-iron(o) and of Bis(benzonitrile)dichloropalladium(II)in Benzene" J Chem Soc, Dalton Trans, 1974, pp. 1521-1524.
Melpolder and Heck, "A Palladiium-Catalyzed Arylation of Allylic Alcohols with Aryl Halides", J. Org. Chem. 1976, vol. 41, pp. 265 265-272.

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