7579-40-0

Usage

InChI:InChI=1/C14H11ClO2/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 103-83-3 N,N'-dimethylbenzylamine 
• 610-96-8 methyl chlorobenzoate 
• 100-44-7 benzyl chloride 
• 118-91-2 ortho-chlorobenzoic acid 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 103-82-2 phenylacetic acid 
• 89-98-5 2-chloro-benzaldehyde 
• 609-65-4 o-chlorobenzoyl chloride 
• 58824-52-5 α-vinyl-o-chlorobenzyl alcohol 
• 108-88-3 toluene 

Downstream Products

• 118-91-2 ortho-chlorobenzoic acid 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 713-36-0 2-benzyltoluene 

Relevant academic research and scientific papers

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.

Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions

A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Direct, rapid and convenient synthesis of esters and thioesters using PPh3/N-chlorobenzotriazole system

We have developed an efficient method for esterification and thioesterification of various carboxylic acids with different alcohols and thiols using PPh3/N-chlorobenzotriazole mixed reagent in CH2Cl2 at room temperature.

Convenient esterification of carboxylic acids by SN2 reaction promoted by a protic ionic-liquid system formed in situ in solvent-free conditions

The reaction of esterification of benzoic acid with benzyl chloride was chosen as a model reaction to study the esterification by SN2 promoted by tertiary amine as deprotonating agent. The use of ionic liquid (IL) 1,3-dimethylimidazolium methanesulfonate [MMIm][OMs] as reaction medium has proven to give quantitative yield of the ester, but interestingly the reaction does occur even in solvent-free conditions, where the acid + the amine form a liquid system (a protic IL) in situ. This last methodology was extended to several carboxylic acids in conditions of atom economy (i.e., without excess of any reagent), giving moderately good yields of esters (54-78%) recovered by weight in pure form.

Electrogenerated N-heterocyclic carbene in ionic liquid: An insight into the mechanism of the oxidative esterification of aromatic aldehydes

An N-heterocyclic carbene (NHC), generated by cathodic reduction of BMIm BF4, mediates the oxidative esterification of aromatic aldehydes with organic bromides in the corresponding ionic liquid as solvent. The product recovery by simple extractive work-up with diethyl ether allowed the ionic liquid to be recycled up to 9 times for subsequent electrolyses, with no significant loss in the product yield. The isolation of an intermediate, whose structure was confirmed by synthesis and transformation into the ester, provided the key for a mechanistic insight into the reaction.

Palladium-catalyzed benzylation of carboxylic acids with toluene via benzylic C-H activation

Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C-H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.

Solvent-free alkylation of N-heteroaromatic compounds by RCOOH-Pb(OAc) 4 system

The solvent-free decarboxylation of carboxylic acids by Pb(OAc)4 affords alkyl radicals, which alkylate 4-methylpyridine, quinoline, and 4-methylquinoline protonated with 2-chlorobenzoic acid. Mechanical activation is required for pyrazine alky

Esterification of carboxylic acids with alcohols under microwave irradiation in the presence of zinc triflatet

The esterification of aliphatic and aromatic carboxylic acids with various alcohols (1°, 2°, 3°, benzylic) was studied under microwave irradiation in the presence of zinc triflate as catalyst; the reaction times were short and the yield of reactions was good to excellent.