16271-22-0

Upstream product

• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 
• 74-95-3 1,1-dibromomethane 
• 4397-14-2 4-(hydroxymethyl)-2,6-dimethylphenol 
• 2233-18-3 4-hydroxy-3,5-dimethylbenzaldehyde 
• 83037-98-3 (4-methoxy-3,5-dimethylphenyl)methanol 
• 5384-21-4 bis(4-hydroxy-3,5-dimethylphenyl)methane 
• 74-88-4 methyl iodide 
• 1426391-40-3 [bis(4-methoxy-3,5-dimethylphenyl)]methyl bis(p-tolyl)methyl ether 
• 1426391-38-9 [bis(4-methoxy-3,5-dimethylphenyl)]methyl diphenylmethyl ether 
• 1426391-31-2 bis[bis(4-methoxy-3,5-dimethylphenyl)methyl] ether 
• 1426391-39-0 [bis(4-methoxy-3,5-dimethylphenyl)]methyl (phenyl)(p-tolyl)methyl ether 
• 885-77-8 4,4'-dimethylbenzhydrol 
• 1426391-61-8 bis(4-methoxy-3,5-dimethylphenyl)methanol 
• 1517-63-1 4-methylphenyl(phenyl)methanol 

Downstream Products

• 110047-35-3 4,4’-dimethoxy-3,3’,5,5’-dimethylbenzophenone 
• 16271-23-1 2,2'-Bis(chloromethyl)-4,4'-dimethoxy-3,3',5,5'-tetramethyldiphenylmethane 

Relevant academic research and scientific papers

Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media

We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.

Crystal structures and isometricity comparison of methylated bisphenol F derivatives

The syntheses and X-ray structures of three methylated bisphenol F derivatives and one respective analogue are reported. A special emphasis lies on the influence of methyl groups on the conformation of the common diphenylmethane scaffold. The introduction of four methyl groups to bisphenol F was found not to disturb its typical strong hydrogen bond network, and yet, to change the pattern of the aromatic interactions in the overall packing. According to the isometricity comparison, the addition of methyl groups to the diphenylmethane core has a greater influence on the conformation of the individual molecules, than the presence or absence of hydrogen bonding donors or acceptors.

Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions

Iodine was demonstrated to be an efficient catalyst for disproportionation of aryl-substituted ethers under solvent-free reaction conditions. Variously substituted 1,1,1′,1′-tetraaryldimethyl ethers were transformed into the corresponding diarylketone and diarylmethane derivatives. I 2-catalyzed transformation of 4-methoxyphenyl substituted ethers yielded mono- and dialkylated Friedel-Crafts products as well. Treatment of trityl alkyl and trityl benzyl ethers with a catalytic amount of iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic studies it was established that a substantial portion of the C-H bond scission took place in the rate-determining step, while the carbonyl oxygen atom originated from the starting ether, and not from the air. The transformation took place under air and under argon, and HI was not a functioning catalyst.