703-02-6

Upstream product

• 57458-01-2 4a-methyl-octahydro-naphthalen-2-one 
• 826-56-2 4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 51417-19-7 4,4a,5,6,7,8-hexahydro-4a-methyl-4-carboxy-2(3H)-naphthalenone 
• 37709-42-5 1-methyl-2-oxocyclohexane-1-carbaldehyde 
• 67-64-1 acetone 
• 83181-15-1 2-Methyl-2-(3'-oxo-1'-butenyl)cyclohexanone 

Downstream Products

• 4242-05-1 1-Hydroxy-4-methyl-5,6,7,8-tetrahydro-naphthalin 
• 3718-79-4 5,6,7,8-tetrahydro-4-methyl-2-naphthalenol 

Relevant academic research and scientific papers

Diels-Alder Reactions of a Bicyclic, Cross-Conjugated Dienone

Aluminium chloride catalyzed Diels-Alder reactions of a bicyclic dienone of the 2,5-cyclohexadienone type with 1,3-butadiene, isoprene, and (E)-piperylene are described.Structure analysis of the adducts by NMR spectroscopy is presented.The site selectivity and face diastereoselectivity of the reactions are discussed.

The Synthesis of 4-Methylcyclohexa-2,5-dienones from Phenols

4-Alkyl phenols have been converted by a known sequence into 2-aryloxyisobutyric acids and thence, by bromination at the 4-position of the aromatic ring with concomitant intramolecular lactone formation, into masked 4-alkyl-4-bromocyclohexa-2,5-dienones.Reaction with lithium dimethylcuprate, as a model for other lithium dialkylcuprates, replaces the bromine by a methyl group.Hydrolytic demasking gives 4-alkyl-4-methylcyclohexa-2,5-dienones.The method should allow the general synthesis of 4-alkylated cyclohexa-2,5-dienones from phenols via a nucleophilic alkylation step.This contrasts with an existing route which uses electrophilic alkylation of phenols or phenoxide ions by a restricted range of reactive alkylating agents.