27749-08-2

Upstream product

• 109-99-9 tetrahydrofuran 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 82763-46-0 4-Methoxy-benzoic acid 4-[ethyl-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-butyl ester 
• 1352060-73-1 δ-cyanobutyl 4-methoxybenzoate 

Relevant academic research and scientific papers

Synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by ZnO

An efficient method for the synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by nano-ZnO under solvent-free condition at room temperature was described. The method is compatible with a range of ethers including tricyclic ethers, tetracyclic ethers, pentacyclic ethers and hexacyclic ethers and have afforded the products with moderate to good yields. The ZnO could be reused up to three times and the product yield after three cycles is 87%.

Palladium(II) acetate catalyzed acylative cleavage of cyclic and acyclic ethers under neat conditions

During the development of a palladium catalyzed C–H activation cross-coupling reaction involving acyl halides, it was noted that palladium(II) acetate catalyzes the acylative cleavage of tetrahydrofuran (used as a solvent) at room temperature to afford the corresponding 4-chlorobutyl ester derivative. After optimization, the reaction was shown to work well with epoxides, oxetane and tetrahydrofuran, but only barely with oxanes at room temperature. Acyclic ethers systematically failed to react under similar conditions, but underwent complete conversion in a microwave reactor at 100 °C.

An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism

A method involving iron catalyzed acylative cleavage of cyclic and acyclic ethers with acyl/aroyl chlorides has been studied to produce chloroesters and esters respectively. Examination of the scope revealed that less electron rich alkyl group in unsymmetric, acyclic ether was acylated while the chloride derived from the counterpart moiety was volatile and difficult to isolate. In contrast, α-branched cyclic ethers were converted to the corresponding primary ester and secondary chloride. Steric hindrance of ether also plays an important role in acylative C-O bond cleavage. The mechanism of ether cleavage is proposed to involve a single electron initiated SN1 dissociative pathway.

Synthesis of δ- And ε-cyanoesters by zinc-catalyzed ring-opening of cyclic ethers with acid chlorides and subsequent cyanation

In the present study, the zinc-catalyzed cleavage of cyclic ethers with acid halides as nucleophiles to yield chloroesters with different chain length has been investigated in detail. In the presence of straightforward and commercially available zinc salts as pre-catalysts excellent yields and selectivities were feasible. After studying the reaction conditions and the scope of the method, several efforts were carried out to understand the reaction mechanism. The obtained chloroesters were subsequently converted to δ- and ε-cyano esters, which are useful precursors in natural product synthesis. Graphical Abstract: [Figure not available: see fulltext.]

Acylative cleavage of ethers with ZnCl2

Acylative cleavage of common ether solvents with ZnCl2 was reported. Different substituted acyl chlorides were reacted with the common ether solvents in the presence of ZnCl2 to obtain the corresponding substituted benzoate.

Rhenium complex-catalyzed acylative cleavage of ethers with acyl chlorides

It was found that rhenium complex was an efficient catalyst for the acylative cleavage of C-O bond of ethers with acyl chlorides. When acyclic ethers were allowed to react with acyl chlorides in the presence of a catalytic amount of ReBr(CO)5, acylative cleavage of C-O bond of acyclic ethers smoothly proceeded to give the corresponding esters in moderate to good yields. Similarly, cyclic ethers were acylative cleaved by acyl chlorides to give the corresponding chloro substituted esters in good yields by the use of Re 2O7 catalyst.

Single-pot conversion of an acid to the corresponding 4-chlorobutyl ester

A single pot conversion of carboxylic acids into the corresponding 4-chlorobutyl esters has been achieved by a novel procedure. The intermediate acid chlorides are not isolated. The double bond and aromatic methoxy group survive the mild reaction conditions. In almost all the examples studied the products are purified by simple flash chromatography.

Non-Catalyzed Cleavage Reactions of Ethers with Acyl Halides under High-Pressure Conditions

Various cyclic and acyclic ethers are efficiently cleaved with acyl chlorides or bromides to give ω-chloro- or ω-bromoesters under high-pressure conditions.