Preparation of menaquinones
AssigneeThe Regents of the University of California
InventorsHenry Rapoport, Clinton D. Snyder
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Abstract
3-Prenyl-substituted menaquinones are made by reacting a 3-metalo-2-alkyl-1,4-di(alkoxy or aralkoxy) naphthalene with a prenyl halide, and then oxidizing the resulting 3-prenyl-2-alkyl-1,4-di(alkoxy or aralkoxy) naphthalene to prepare the corresponding 3-prenyl-substituted menaquinone. The metallo substituent at the 3-position may be Li, Li/Cu, Cu or MgBr. The oxidation is advantageously conducted by the use of argenic oxide.
Claims22
A method of preparing menaquinones of the formula ##STR4## wherein R is lower alkyl, Z is --CH.sub.2 CH.dbd.C(CH.sub.3)CH.sub.2 ].sub.m, --CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 ].sub.n, or combinations thereof, and in which each of m and n, and their sum is 0 to about 12, comprising reacting at a temperature of about 5 to 60.degree. C. 3-metallo naphthalene of the formula ##STR5## wherein R.sub.1 and R.sub.2 are lower alkyl, or monocyclic, hydrocarbyl aralkyl of 7 to about 12 carbon atoms, and M is selected from the group consisting of Li, (CuLi).sub.1/2, MgBr and Cu, with prenyl halide of the formula
- X--CH.sub.2 CH .dbd. C(CH.sub.3) CH.sub.2 --Z -- H
- wherein X is halogen, to provide 1,4-diether naphthalene of the formula ##STR6## oxidizing the 1,4-diether naphthalene to produce the corresponding menaquinone.
A method of preparing 1,4-diether naphthalene of the formula ##STR7## wherein R is lower alkyl, R.sub.1 and R.sub.2 are lower alkyl, or monocyclic, hydrocarbyl aralkyl of 7 to about 12 carbon atoms, and Z is --CH.sub.2 CH.dbd.C(CH.sub.3)CH.sub.2 ].sub.m, --CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 ].sub.n, or combinations thereof, and in which each of m and n, and their sum is 0 to about 12, comprising reacting at a temperature of about 5 to 60.degree. C. 3-metallo naphthalene of the formula ##STR8## wherein M is selected from the group consisting of Li, (CuLi).sub.1/2, MgBr, and Cu, with prenyl halide of the formula
- X--CH.sub.2 CH .dbd. C(CH.sub.3)CH.sub.2 --Z-- H
- wherein X is halogen, to provide the 1,4-diether naphthalene.
Dependencies are inferred from the claim text.