4501-52-4

Upstream product

• 106-42-3 para-xylene 
• 953-91-3 cyclohexyl tosylate 
• 110-83-8 cyclohexene 
• 100793-20-2 2-Bromomethyl-benzoic acid cyclohexyl ester 
• 538-75-0 dicyclohexyl-carbodiimide 
• 71-43-2 benzene 
• 4351-54-6 cyclohexyl formate 
• 108-93-0 cyclohexanol 
• 16156-56-2 cyclohexyl mesylate 
• 7446-70-0 aluminium trichloride 
• 542-18-7 cyclohexyl chloride 
• 98-95-3 nitrobenzene 
• 60260-74-4 (methylsulfonyl)cyclohexane 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 2523-39-9 3-methylfluorene 
• 1314905-81-1 (E)-4-(2,5-dimethyl-4-cyclohexylphenyl)-4-oxo-2-butenoic acid 
• 95-87-4 2,5-Dimethylphenol 
• 108-94-1 cyclohexanone 
• 92254-03-0 5-methyl-[1,1'-biphenyl]-2-carboxylic acid 

Relevant academic research and scientific papers

Friedel-Crafts Cyclohexylation of Arenes with 1,3-Dicyclohexylcarbodiimide (DCC)

The reaction of arenes with 1,3-dicyclohexylcarbodiimide in the presence of concentrated sulfuric acid or anhydrous aluminum chloride gave the corresponding cyclohexylated arenes in good yields.

Development of highly efficient Friedel-Crafts alkylations with alcohols using heterogeneous catalysts under continuous-flow conditions

The development of Friedel-Crafts alkylations with alcohols under continuous-flow conditions using heterogeneous catalysts is reported. The reactivities and durabilities of the examined catalysts were systematically investigated, which showed that montmorillonite clay is the best catalyst for these reactions. A high turnover frequency of 9.0 × 102h?1was recorded under continuous-flow conditions, and the continuous operation was successfully maintained over one week.

Iron-catalyzed arene alkylation reactions with unactivated secondary alcohols

A simple, iron-based catalytic system allows for the inter- and intramolecular arylation of unactivated secondary alcohols. This transformation expands the substrate scope beyond the previously required activated alcohols and proceeds under mild reaction conditions, tolerating air and moisture. Furthermore, the use of an enantioenriched secondary alcohol provides an enantioenriched product for the intramolecular reaction, thereby offering a convenient approach to nonracemic products.

Versatile friedel-crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system

A variety of molybdenum complexes catalyze Friedel-Crafts-type alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)6] and two equivalents of o-chloranil catalytically furnished the hydroarylation product of norbornene with p-xylene at 80°C, whereas [Cr(CO)6] and [W(CO)6] failed to catalyze the same reaction, thus indicating the importance of the molybdenum source. The best results were obtained when a molybdenum(II) complex [CpMoCl(CO)3] (Cp = cyclopentadienyl) was used as a precatalyst. The hydroarylation reactions also took place with styrenes, cyclohexenes, and 1 -hexene as olefin substrates. The electrophilic-substitution mechanism was proposed on the basis of the ortho/para selectivities and the Markovnikov selectivities observed for the hydroarylation products. Our hypothesis was further corroborated by the fact that in the presence of the [CpMoCl(CO)3]/o-chloranil catalytic system, secondary, benzylic, or allylic alcohols participated in the alkylation of benzenes with similar selectivities.

Nitrosonium salts, NO+X- (X = B(3,5-diCF 3Ph)4- or PW12O40 3-), as electrophilic catalysts for alkene activation in arene alkylation and dimerization reactions

It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O403-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C. Copyright

Alkylation on graphite in the absence of Lewis acids

Graphite is introduced as a convenient catalyst for alkylation of aromatic compounds and alcohols by benzyl, tertiary alkyl, and secondary alkyl halides in the absence of strong Lewis acids. Primary alkyl halides are not active under the reaction conditions.

An efficient method for aromatic Friedel-Crafts alkylation, acylation, benzoylation, and sulfonylation reactions

Aromatic electrophilic substitution reactions such as alkylation, acylation, benzoylation, and sulfonylation were studied in the presence of a catalytic amount of Cu(OTf)2 and Sn(OTf)2. Cu(OTf)2 was very efficient for alkylation, acylation, and benzoylation reactions. However, in case of sulfonylation reactions, Sn(OTf)2 gave better results.

Liquid-phase catalytic oxidation of 2,5-dimethylbiphenyl

Liquid-phase catalytic oxidation of 2,5-dimethylbiphenyl provided 2,5-biphenyldicarboxylic acid. The effect on reaction of temperature, catalyst type, and reagents concentration was investigated.

A new convenient Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates in the presence of scandium(III) trifluoromethanesulfonate or trifluoromethanesulfonic acid as the catalyst

Scandium(III) triflate and triflic acid were both found to be efficient catalysts for the Friedel-Crafts alkylation of aromatic compounds using methanesulfonates derived from secondary alcohols as alkylating agents.

Scandium(III) trifluoromethanesulfonate-catalyzed Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates

Scandium(III) inflate was found to be an efficient catalyst for the Friedel-Crafts alkylation of aromatic compounds with methanesulfonates derived from secondary alcohols; the catalyst can be reused without a significant loss of activity.