73640-02-5

Upstream product

• 67-56-1 methanol 
• 92428-43-8 O-Benzoyl-mandelsaeurechlorid 
• 101-41-7 benzeneacetic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 65-85-0 benzoic acid 
• 18793-81-2 methyl 2-phenyl-2-(2-tosylhydrazono)acetate 
• 32569-87-2 4-methoxyl-phenylacetylene 
• 4358-87-6 (RS)-methyl mandelate 
• 98-88-4 benzoyl chloride 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 614-45-9 tert-Butyl peroxybenzoate 

Downstream Products

• 92428-43-8 O-Benzoyl-mandelsaeurechlorid 
• 115061-56-8 O-benzoylmandelic acid 

Relevant academic research and scientific papers

Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids

Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).

Blue Light-promoted Carbene Transfer Reactions of Tosylhydrazones

Metal-free photochemical carbene-transfer reactions of tosylhydrazones were developed under blue light irradiation at room temperature. This reaction constructs C?X (X=C, N, O, S) bonds and cyclopropanes from readily available and stable starting material

One-Pot Reaction of Carboxylic Acids, Ynol Ethers, and m-CPBA for Synthesis of α-Carbonyloxy Esters

A novel one-pot reaction of carboxylic acids, ynol ethers, and m-CPBA for the synthesis of α-carbonyloxy esters in the presence of Ag2O is described. This process provides a direct approach to α-carbonyloxy esters with the achievement of format

Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols

Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.

A phosphetane catalyzes deoxygenative condensation of α-keto esters and carboxylic acids via PIII/PV=O redox cycling

A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling. The importance of ring strain in the phosphacyclic catalyst is substantiated by an observed temperature-dependent product selectivity effect. The results point to an inherent distinction in design criteria for organophosphorus-based catalysts operating via PIII/PV=O redox cycling as opposed to Lewis base (nucleophilic) catalysis.

Copper-catalyzed benzylic oxidation of C(sp3)-H bonds

A selective oxidation of benzylic C(sp3)-H bonds to C(sp 3)-O bonds catalyzed by copper complexes of quinoline-imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C-H bond functionalization.

Photochemistry of Diaryl Vicinal Tetraketones and Chemistry of Intermediate (Aroyloxy)arylketenes

Photolysis of diaryl vic-tetraketones results in formation of tricyclic-γ-lactones 3 and 4 with low quantum but high chemical yield. (Aroyloxy)arylketenes and carbon monoxide are the initial photochemical products of these photolyses. Subsequent reaction of ketene with ground-state tetraketone results in formation of the observed photoproducts via intermediate β-lactones. The latter are formed with a high degree of stereoselectivity. The failure of a cyclic tetraketone to react is attributed to its inability to undergo the cyclic mechanism proposed for formation of ketenes from tetraketones. Dimesityl and di-tert-butyl tetraketones react by a competing intramolecular hydrogen atom transfer mechanism. Dimerization of (benzoyloxy)phenylketene and its reactions with a number of tetraketones are described.