Production of alkoxynaphthyl-substituted ketones from naphthalde

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

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C07C 4545

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active

058615385

ABSTRACT:
A mixture formed from an alkoxy-2-naphthaldehyde (e.g., 6-methoxy-2-naphthaldehyde), acetone, and aqueous NaOH and/or KOH is heated at about 20.degree. to about 56.degree. C. for about 0.25 to about 2 hours such that the conversion of monoalkoxy-substituted 2-naphthaldehyde is at least 97% and the yield of (alkoxy-substituted 2-naphthyl)-3-buten-2-one is at least 95% based on the monoalkoxy-substituted 2-naphthaldehyde used in forming the mixture. The (alkoxy-substituted 2-naphthyl)-3-buten-2-one can be hydrogenated using, for example, a Pd/C catalyst to form the corresponding saturated ketone. The process enables efficient production of precursors of nabumetone and related pharmaceuticals by a clean, highly efficient reaction.

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patent: 4270004 (1981-05-01), Rose et al.
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patent: 5214151 (1993-05-01), Nakajima et al.
patent: 5300654 (1994-04-01), Nakajima et al.
Fieser, Louis F. et al., Organic Chemistry (1944), pp. 700-701.

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