61597-37-3

Usage

Uses

Used in Pharmaceutical Industry:
4-methoxy-alpha,alpha-dimethylcyclohexa-1,4-diene-1-methanol is used as a key intermediate in the production of labelled Nabilone, a synthetic cannabinoid used for medicinal purposes. Its unique structure allows for the development of radiolabelled compounds, which are essential for research and diagnostic applications in the field of drug development and medical imaging.

InChI:InChI=1/C10H16O2/c1-10(2,11)8-4-6-9(12-3)7-5-8/h4,7,11H,5-6H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 7428-99-1 2-(4-methoxyphenyl)propan-2-ol 
• 7664-41-7 ammonia 

Downstream Products

• 56496-90-3 dl-trans-1-hydroxy-3-(1,1-dimethyl-heptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one 
• 72912-59-5 4-(2-hydroxy-2-propyl)-cyclohex-3-en-1-one 
• 83889-48-9 9,11-β-epoxy-11-tosyl-6a,10a-trans-HHC 
• 83889-48-9 9,11-α-epoxy-11-tosyl-6a,10a-trans-HHC 
• 25952-85-6 11-hydroxy-6a,10a-trans-Δ⁸-THC 
• 53865-18-2 11-oxo-6a,10a-trans-Δ⁸-THC 
• 52663-85-1 11-oxo-6a,10a-trans-Δ⁹-THC 
• 28623-60-1 (+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 64317-84-6 4-(1-methylethylidene)cyclohex-2-en-1-one 
• 6616-69-9 11-nor-9-keto-6a,10a-cis-HHC 

Relevant academic research and scientific papers

IMPROVED SYNTHESIS OF HEXAHYDRODIBENZOPYRANONES

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.

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

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.

2,6-Methano-2H-1-benzoxocins

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.