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US 3,948,958 AGranted
Process for making 3-prenylated menaquinones and ether intermediates
AssigneeThe Regents of the University of California
InventorsHenry Rapoport, Clinton D. Snyder
Life of this patent
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Abstract
3-Prenyl-substituted-2-alkyl menaquinones are made by reacting an alkali metal salt of a 3-alkyl-4-alkoxy or aralkoxy-1-naphthol with a prenyl halide, and oxidizing the resulting 2-prenyl-3-alkyl-4-alkoxy or aralkoxy-1-naphthol to the corresponding 3-prenyl-substituted-2-alkyl menaquinone. There is also disclosed a procedure for making the alkali metal salts involving the preparation of an ether-ester and hydrogenolysis.
Claims23
A method of preparing menaquinones of the formula ##SPC8##
- wherein R is lower alkyl and Z is --CH.sub.2 CH = C(CH.sub.3)CH.sub.2--m, --CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2--n, or combinations thereof, and in which each of m and n, and their sum, is 0 to about 12, comprising reacting alkali metal salt of the formula ##SPC9##
- wherein R.sub.4 is lower alkyl or monocyclic hydrocarbon aralkyl of 8 to about 12 carbon atoms having at least two carbon atoms in the chain directly between the fused ring and the aryl group of the aralkyl, and M is alkali metal, with prenyl halide of the formula
- X--CH.sub.2 CH = C(CH.sub.3)CH.sub.2-- Z--H
- wherein X is halogen, to provide prenylated 1-naphthol of the formula ##SPC10##
- oxidizing the prenylated 1-naphthol to produce the corresponding menaquinone.
2 more elements
A method of preparing prenylated 1-naphthol of the formula ##SPC11##
- wherein R is lower alkyl, R.sub.4 is lower alkyl or monocyclic hydrocarbon aralkyl of 8 to about 12 carbon atoms having at least two carbon atoms in the chain directly between the fused ring and the aryl group of the aralkyl, and Z is --CH.sub.2 CH = C(CH.sub.3)CH.sub.2--m, --CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2--n, or combinations thereof, and in which each of m and n, and their sum, is 0 to about 12, comprising reacting alkali metal salt of the formula ##SPC12##
- wherein M is alkali metal, with prenyl halide of the formula
- X--CH.sub.2 CH = C(CH.sub.3)CH.sub.2 --Z-H
- wherein X is halogen, to provide prenylated 1-naphthol.
1 more element
Dependencies are inferred from the claim text.