889-24-7

Upstream product

• 831-78-7 3-(3,5-dimethoxyphenyl)-1-bromopropane 
• 996-82-7 sodium diethylmalonate 
• 64-19-7 acetic acid 
• 202654-80-6 1-(3,5-dimethoxyphenyl)octane-5,7-dione 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 1080-05-3 3-(3,5-dimethoxyphenyl)-1-propanol 
• 20767-04-8 (E)-3,5-dimethoxycinnamic acid 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 886-51-1 Methyl 3-(3',5'-dimethoxyphenyl)propionate 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 730-01-8 2-(3',5'-Dimethoxyphenyl)-ethane-1,1-dicarboxylic acid 

Relevant academic research and scientific papers

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.

Radical-mediated cyclisation of ω-aryl-β-dicarbonyl compounds to tetrahydrobenzocyclohepten-6-ones, hexahydrobenzocycloocten-6-ones and naphthalen-2(1H)-ones

Manganese(III) acetate in acetic acid promotes efficient radical-mediated oxidative cyclisation of ε-aryl-β-dicarbonyl and Z-γ,δ-unsaturated δ-aryl-β-dicarbonyl compounds carrying electron-releasing groups in the aromatic ring, forming 6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ones and naphthalen-2(1H)-ones, respectively. The process is accompanied by secondary acetoxylation at the activated benzylic position of the initial cyclisation products, and is exemplified by the conversions of the ε- and δ-aryl-β-dicarbonyl compounds 6 and 11 into the benzocycloheptenone 18 and the naphthalenone 21, respectively. Application of the oxidation to the formation of 8-membered hexahydro- and tetrahydro-benzocycloocten-6-ones 19 and 22 from ζ-aryl-β-dicarbonyl and Z-γ,δ-unsaturated ζ-aryl-β-dicarbonyl compounds is limited by low reactivity, and in the latter case, by radical rearrangement followed by cyclisation to a tetralin.