41978-29-4

Upstream product

• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 108-95-2 phenol 
• 82246-94-4 4-(1-Hydroxy-2-phenoxy-ethyl)-phenol 

Downstream Products

• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Two-Step, Catalytic C-C Bond Oxidative Cleavage Process Converts Lignin Models and Extracts to Aromatic Acids

We herein report a two-step strategy for oxidative cleavage of lignin C-C bond to aromatic acids and phenols with molecular oxygen as oxidant. In the first step, lignin β-O-4 alcohol was oxidized to β-O-4 ketone over a VOSO4/TEMPO [(2,2,6,6-tetramethylpiperidin-1-yl)oxyl)] catalyst. In the second step, the C-C bond of β-O-4 linkages was selectively cleaved to acids and phenols by oxidation over a Cu/1,10-phenanthroline catalyst. Computational investigations suggested a copper-oxo-bridged dimer was the catalytically active site for hydrogen-abstraction from Cβ-H bond, which was the rate-determining step for the C-C bond cleavage.

Gas-phase fragmentation of deprotonated p-hydroxyphenacyl derivatives

Electrospray ionization of methanolic solutions of p-hydroxyphenacyl derivatives HO-C6H4-C(O)-CH2-X (X = leaving group) provides abundant signals for the deprotonated species which are assigned to the corresponding phenolate anions -O-C6H 4-C(O)-CH2-X. Upon collisional activation in the gas phase, these anions inter alia undergo loss of a neutral "C 8H6O2" species concomitant with formation of the corresponding anions X-. The energies required for the loss of the neutral roughly correlate with the gas phase acidities of the conjugate acids (HX). Extensive theoretical studies performed for X = CF3COO in order to reveal the energetically most favorable pathway for the formation of neutral "C8H6O2" suggest three different routes of similar energy demands, involving a spirocyclopropanone, epoxide formation, and a diradical, respectively.