52041-27-7

Upstream product

• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 

Downstream Products

• 52041-31-3 Acetic acid 2'-{2-acetoxy-5-[1-acetoxy-2-(2,6-dimethoxy-phenoxy)-ethyl]-3-methoxy-phenoxy}-5,5'-bis-[1-acetoxy-2-(2,6-dimethoxy-phenoxy)-ethyl]-3,3'-dimethoxy-biphenyl-2-yl ester 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 61413-50-1 1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol 
• 52041-24-4 1-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-2-(2,6-dimethoxyphenoxy)ethane 

Relevant academic research and scientific papers

Singlet oxygen in the photodegradation of lignin models

The photochemical oxidation of lignin models in the presence of singlet oxygen was studied. The treatment of the non-phenolic β-O-4 aryl ether derivatives 6, 7, and 8 in the presence of both oxygen and Rose Bengal gave products deriving from a formal β-C-O cleavage formation. By this way. the derivatives 12, 13, and 15 were obtained. The photochemical oxidation of the phenolic β-O-4 aryl ether 9 gave the same type of product confirming that, in this case, the presence of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone call occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the molecule.

Thio-assisted reductive electrolytic cleavage of lignin β-O-4 models and authentic lignin

Avoiding the use of expensive catalysts and harsh conditions such as elevated temperatures and high pressures is a critical goal in lignin depolymerization and valorization. In this study, we present a thio-assisted electrocatalytic reductive approach using inexpensive reticulated vitreous carbon (RVC) as the working cathode to cleave the β-O-4-type linkages in keto aryl ethers. In the presence of a pre-electrolyzed disulfide (2,2′-dithiodiethanol) and a radical inhibitor (BHT) at room temperature at a current density of 2.5 mA cm-2, cathodic reduction of nonphenolic β-O-4 dimers afforded over 90% of the corresponding monomeric C-O cleavage products in only 1.5 h. Extended to DDQ-oxidized poplar lignin, this combination of electric current and disulfide, applied over 6 h, released 36 wt% of ethyl acetate soluble fragments and 26 wt% of aqueous soluble fragments, leaving only 38 wt% of insoluble residue. These findings represent a significant improvement over the current alone values (24 wt% ethyl acetate soluble; 22 wt% aqueous soluble; 54 wt% insoluble residue) and represent an important next step in our efforts to develop a mild electrochemical method for reductive lignin deconstruction.