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 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 100-53-8 phenylmethanethiol 
• 2902-69-4 2,2,2-trichloroacetophenone 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.

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.