76841-70-8

Upstream product

• 592-41-6 1-hexene 
• 614-45-9 tert-Butyl peroxybenzoate 
• 928-95-0 (E)-2-Hexen-1-ol 
• 93-97-0 benzoic acid anhydride 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 65-85-0 benzoic acid 
• 100-53-8 phenylmethanethiol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1192690-71-3 C₉H₁₆O₃ 
• 72128-64-4 1-phenyl-3-propyl-pent-4-en-1-one 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of thiols, alcohols, and oxygen for the synthesis of esters

Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions.

Divergent synthesis of (6S,1′S,2′R)-hydroxypestalotin via tandem conjugate addition-lactonization sequence

The stereoselective synthesis of (6S,1′S,2′R)-hydroxypestalotin from trans-hex-2-en-1-ol utilizing asymmetric dihydroxylation and Luche's reduction and tandem conjugative addition-lactonization as the key steps is reported.

Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids

This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.

Organocatalytic selective benzoylation of alcohols with trichloromethyl phenyl ketone: Inverse selectivity in benzoylation of alcohols containing phenol or aromatic amine functionality

Trichloromethyl phenyl ketone benzoylates primary and secondary aliphatic alcoholic groups in compounds also containing a phenolic group in the presence of 2-10 mol % of PMDETA organocatalyst at room temperature in high yields and excellent selectivity. It also shows the potential to selectively benzoylate primary alcoholic groups of aminoarylalkanols and primary-secondary diols as well as primary amino group of alkyl amines in the presence of aryl amines under similar conditions. A rationale for the selectivity and efficiency of the reaction has been provided.

On the role of triflic acid in the metal triflate-catalysed acylation of alcohols

The acylation of alcohols by anhydrides, catalysed by a wide range of metal triflates, is a powerful and mild method for the preparation of a variety of esters. Mechanistic insights demonstrate that triflic acid is generated under these reaction conditions and that, at least, two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the metal triflate.

Rapid and reusable copper catalytic system for allylic oxidation of olefins in hexafluoroisopropanol as solvent

Cu2O mixed with perfluorododecanoic acid C11F23COOH and t-butyl peroxybenzoate in hexafluoroisopropanol led to a rapid and reusable catalytic system for the Kharasch-Sosnovsky reaction.

Stereoselective Preparation of (E)-Allyl Alcohols via Radical Elimination from anti-γ-Phenylthio-β-nitro Alcohols

Phenylthio and hydroxymethyl groups may be introduced into nitroalkenes stereoselectively by treatment with benzenethiol and aqueous formaldehyde to give anti-γ-phenylthio-β-nitro alcohols, which are converted into (E)-allyl alcohols via radical elimination induced by Bu3SnH.