103437-98-5

Basic information

• Product Name: Benzoic acid, 4-methoxy-, 2-cyclohexen-1-yl ester
• CAS NO: 103437-98-5
• Molecular Formula: C14H16O3
• Molecular Weight: 232.279
• Mol File: 103437-98-5.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-methoxy-, 2-cyclohexen-1-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-methoxy-, 2-cyclohexen-1-yl ester(103437-98-5)
• EPA Substance Registry System: Benzoic acid, 4-methoxy-, 2-cyclohexen-1-yl ester(103437-98-5)

Safety Data

• Hazardous Substances Data: 103437-98-5(Hazardous Substances Data)

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-93-8 p-methylanizole 
• 142-71-2 copper diacetate 
• 3290-99-1 4-methoxybenzoic acid hydrazide 

Downstream Products

• 103438-02-4 c-2,t-3-dibromo-r-1-cyclohexyl p-methoxybenzoate 
• 103530-07-0 t-2,c-3-dibromo-r-1-cyclohexyl p-methoxybenzoate 
• 108345-22-8 trans-3-bromocyclohexano-cis-1,2-(2'-anisyl-1',3'-dioxolan-2'-ylium) tribromide 
• 108345-20-6 4-Methoxy-benzoic acid (1R,2S,6R)-2,6-dibromo-cyclohexyl ester 
• 108393-10-8 4-Methoxy-benzoic acid (1S,2R,3S)-2,3-dibromo-cyclohexyl ester 

Relevant articles and documents

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A dual-functional copper porphyrin-catalyzed cross dehydrogenative coupling (CDC) of carboxylic acids with alkanes was reported firstly. The reaction gives allylic esters or alkylalkenes depending on the carboxylic acid substrates. Copper porphyrin catalyzed CDC method has the superiority of short reaction time, good functional group tolerance, base and solvent free, producing target products in an atom-economic manner.

Copper-iron mixed oxide supported onto cordierite honeycomb as a heterogeneous catalyst in the Kharasch-Sosnovsky oxidation of cyclohexene

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Copper-catalyzed oxidative dehydrogenative functionalization of alkanes to allylic esters

Herein, we report a general, efficient and solvent-free method for the one-pot synthesis of allylic esters via dehydrogenation of unactivated alkanes and subsequent oxidative cross coupling with different substituted carboxylic acids. A simple, well defined and air stable Cu(II)-complex, [Cu(MeTAA)], featuring a tetraaza-macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)) is used as the catalyst. A wide variety of substituted allylic esters were synthesized in high yields starting from readily available starting materials. Control reactions were carried out to understand the reaction sequence and the plausible mechanism.

Copper porphyrin as efficient catalysts for esterification of allyl sp3 C–H bond with carboxylic acid

We described that copper 5,10,15,20-tetrakis (ethoxycarbonyl)porphyrin (TECP) catalyzed oxidative cross dehydrogenative coupling of allyl sp3 C–H bond with acid for the synthesis of allyl esters in a homogeneous system. This reaction proceeded

NHPI- and TBAI-Co-Catalyzed Synthesis of Allylic Esters from Toluene Derivatives and Alkenes

An N -hydroxyphthalimide (NHPI) and tetrabutylammonium iodide (TBAI) co-catalyzed oxidative coupling reaction of toluene derivatives and alkenes has been disclosed. This method can serve as a new strategy to access allylic ester using toluene derivatives as oxyacylating reagent. This metal-free protocol also features the readily available starting materials, broad substrate scope, and mild reaction conditions.

Copper porphyrin catalyzed esterification of C(sp3)-H via a cross-dehydrogenative coupling reaction

The crystal structure of 5,10,15,20-tetra(ethoxycarbonyl)porphyrin copper(ii) showed that its central copper has a six-coordinate structure. An efficient copper porphyrin-catalyzed cross-dehydrogenative coupling (CDC) esterification reaction between C(sp

Iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids: Facile access to allylic esters

The first general and efficient iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids using ionic iron(III) complexes (1–4) as a catalyst and DTBP (DTBP?=?di-tert-butyl peroxide) as an oxidant is achieved. A variety of allylic esters were synthesized in good to excellent yields using the ionic iron(III) complex 2 as a catalyst in a 5?mol% loading. This reaction is characterized by its high efficiency, broad substrate scope with excellent steric hindrance tolerance and good functional group compatibility.

Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds

A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

Copper-catalyzed oxidative coupling of acids with alkanes involving dehydrogenation: Facile access to allylic esters and alkylalkenes

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Copper-catalyzed oxidative dehydrogenative carboxylation of unactivated alkanes to allylic esters via alkenes

We report copper-catalyzed oxidative dehydrogenative carboxylation (ODC) of unactivated alkanes with various substituted benzoic acids to produce the corresponding allylic esters. Spectroscopic studies (EPR, UV-vis) revealed that the resting state of the catalyst is [(BPI)Cu(O2CPh)] (1-O2CPh), formed from [(BPI)Cu(PPh3)2], oxidant, and benzoic acid. Catalytic and stoichiometric reactions of 1-O2CPh with alkyl radicals and radical probes imply that C-H bond cleavage occurs by a tert-butoxy radical. In addition, the deuterium kinetic isotope effect from reactions of cyclohexane and d12-cyclohexane in separate vessels showed that the turnover-limiting step for the ODC of cyclohexane is C-H bond cleavage. To understand the origin of the difference in products formed from copper-catalyzed amidation and copper-catalyzed ODC, reactions of an alkyl radical with a series of copper-carboxylate, copper-amidate, and copper-imidate complexes were performed. The results of competition experiments revealed that the relative rate of reaction of alkyl radicals with the copper complexes follows the trend Cu(II)-amidate > Cu(II)-imidate > Cu(II)-benzoate. Consistent with this trend, Cu(II)-amidates and Cu(II)-benzoates containing more electron-rich aryl groups on the benzamidate and benzoate react faster with the alkyl radical than do those with more electron-poor aryl groups on these ligands to produce the corresponding products. These data on the ODC of cyclohexane led to preliminary investigation of copper-catalyzed oxidative dehydrogenative amination of cyclohexane to generate a mixture of N-alkyl and N-allylic products.