70264-59-4Relevant academic research and scientific papers
Ipso-chlorination of para-alkylphenols ethers with SbF5-CH2Cl2 (CHCl3, CCl4): a novel route to 4-chlorocyclohexa-2,5-dienones
Jouannetaud, Marie-Paule,Jacquesy, Jean-Claude,Karam, Omar,Coustard, Jean-Marie,Ferron, Bruno
, p. 284 - 290 (2007/10/02)
Chlorination of mono or polycyclic para-alkylphenols ethers with SbF5-CH2Cl2 (CHCl3, CCl4) gives the corresponding 4-chlorocyclohexa-2,5-dienones in a better yield than reaction with SbCl5-CH2Cl2(SO2).The postulated mechanism implies electrophilic chlorin
Ipso-Chlorination of 4-Alkylphenols Ethers. A Novel Route to 4-Chlorocyclohexa-2,5-dienones.
Ferron, Bruno,Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Karam, Omar,Coustard, Jean-Marie
, p. 2949 - 2952 (2007/10/02)
Selective chlorination of 4-alkylphenols ethers with SbF5/CH2Cl2 (CHCl3, CCl4) yields 4-chlorocyclohexa-2,5-dienones; no α-chlorination to a carbonyl group is observed in the reaction conditions.
Phenol-Dienone Rearrangement in the Chlorination of p-Cresol with t-Butyl Hypochlorite
Husain, Sajid,Kifayatullah, Mohd
, p. 711 - 714 (2007/10/02)
From the chlorination of p-cresol with t-butyl hypochloride (3 mol) in acetic acid five non-phenolic compounds have been isolated and identified as substituted 2,5-cyclohexadienones (I-V).The formation of these compounds has been explained in terms of phenol-dienone and dienone-phenol rearrangements. 2,6-Dichloro-4-(2-chloro-4-methylphenoxy)-4-methyl-2,5-cyclohexadienone is a condensation product of the intermediate chlorocresols and its mechanistic details have been discussed.
Electrophilic Chlorination of 4-Methylphenols with Molecular Chlorine. Synthesis of Dimethoxy Aromatics by Methanolysis of 4-Chloro-4-methylcyclcohexa-2,5-dienones
Bergquist, Karl-Erik,Nilsson, Anders,Ronlan, Alvin
, p. 675 - 684 (2007/10/02)
The chlorination of p-cresol (1a), 2,4-dimethylphenol (1b), 3,4-dimethylphenol (1c), 2,4,5-trimethylphenol (1d), 2,4,6-trimethylphenol (1e) and the various possible mono- and dichloro derivatives of these phenols (3a-d, 6a and 6 c) with molecular chlorine was investigated in dichloromethane or dimethyl formamide solution.The 2,6-substituted p-cresol derivatives all give quantitative yields of 4-chloro-4-methylcyclohexa-2,5-dienones (5b, 5d, 7a, 7c and 2e), whereas the less substituted p-cresol derivatives give a 20-25percent yield of corresponding 4-chloro-4-methylcyclohexa-2,5-dienones (2a-d, 5a and 5c), the other products being chlorinated phenols.Treatment of 4-chloro-4-methylcyclohexa-2,5-dienones with at least one of the double bonds of the ring unsubstituted (2a-c and 4a) with methanol gave a quantitative yield of a 1,3-dimethoxybenzene derivative (9a-c and 10), whereas similar treatment of 4-chloro-2,4,5-trimethylcyclohexa-2,5-dienone (2d) gave 5-methoxy-2,3-dimethylbenzyl methyl ether (11).Treatment of the other 4-chlorodienones with methanol gave the corresponding 4-methoxydienones.Electrophilic chlorination of certain p-cresol derivatives followed by methanolysis hence is a facile although low-yield method for 3-methoxylation or selective side chain oxidation of these p-cresol derivatives.
