1369802-01-6Relevant academic research and scientific papers
Conversion of Cyclohexanones to Alkyl Aryl Ethers by Using a Pd/C–Ethylene System
El-Deeb, Ibrahim Yussif,Tian, Miaomiao,Funakoshi, Tatsuya,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 409 - 413 (2017/01/24)
The conversion of cyclohexanone and substituted cyclohexanones into alkyl aryl ethers by using a Pd/C–ethylene system is discussed, with ethylene functioning as a hydrogen acceptor. The ether products are easily transformed into the corresponding phenols by treatment with BBr3. The direct conversion of cyclohexenone into phenol in the presence of a catalytic amount of Pd/C under an ethylene atmosphere is also described.
Acid catalyzed alkylation of phenols with cyclohexene: Comparison between homogeneous and heterogeneous catalysis, influence of cyclohexyl phenyl ether equilibrium and of the substituent on reaction rate and selectivity
Ronchin,Vavasori,Toniolo
scheme or table, p. 134 - 141 (2012/03/09)
The reactivity of several phenols toward liquid phase alkylation with cyclohexene in the presence of heterogeneous and homogeneous acid catalyst at 358 K is studied. The comparison between Amberlyst 15 and CH3SO 3H, as examples of heterogeneous and homogeneous systems, shows a higher activity of the former with different behavior of selectivity between the two systems, anyway, in both systems O-alkylation and ring alkylations occur. A remarkable difference in the selectivity of the ring alkylation between heterogeneous and homogeneous systems is observed: Amberlyst 15 shows a constant ortho/para ratio close to 2, while in the presence of CH3SO 3H ortho/para is variable from 3 to 5, suggesting an involvement of the cyclohexyl phenyl ether rearrangement. This is proved also by a direct relationship between the ortho/para ratio and the concentration of the cyclohexyl phenyl ether when CH3SO3H is used as a catalyst. The formation of cyclohexyl aryl ethers is reversible; on the contrary, ring alkylation appears irreversible. The reactivity of the dimethylphenols shows a strong influence of the steric hindrance of the substituent on the electrophilic attack of the cyclohexyl cation, which is poorly influenced by the inductive effect of the methyl group.
