- IMPROVED SYNTHESIS OF HEXAHYDRODIBENZOPYRANONES
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The current application relates to an improved process for the synthesis of a 6a, 10a-cis-hexahydrodibenzo[b,d]pyran-9-one derivative, such as nabilone, by condensing a 5-substituted resorcmol with a 1-alkoxy-4-(1 -hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a Lewis acid selected from triflic anhydride, triflic acid, and sulfuric acid. The starting 1,4-cyclohexadiene derivative is prepared by an improved Birch reduction process in which a benzene derivative is reacted with gaseous ammonia, an alcohol, and an alkaline metal such as lithium, sodium, or potassium.
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Page/Page column 10-11
(2010/04/06)
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- Process for preparing dl-cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-ones
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Reaction of a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst affords the corresponding dl-cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.
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- 2,6-Methano-2H-1-benzoxocins
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Novel 2-oxy-5-isopropylidene-7-hydroxy-9-substituted-2,6-methano-3,4,5,6-tetrahydro-2H-1-benzoxocins are prepared by condensing a 5-(substituted)resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst. The new benzoxocin derivatives are useful in the synthesis of certain dibenzo[b,d]pyran-9-ones, valuable as anti-anxiety, analgesic, and anti-depressant drugs.
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