22400-03-9

Upstream product

• 90-05-1 2-methoxy-phenol 
• 13078-21-2 ethyl 2-(2-methoxyphenoxy)acetate 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 
• 156482-49-4 methyl 3-(4-(benzyloxy)-3-methoxyphenyl)-3-oxopropanoate 

Downstream Products

• 22317-34-6 β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 121-33-5 vanillin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 7382-59-4 erythro-1-(4-Hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 

Relevant academic research and scientific papers

One-pot synthesis of β-O-4 lignin models: Via the insertion of stable 2-diazo-1,3-dicarbonyls into O-H bonds

Because lignin is a macromolecule that is a sustainable source of aromatic compounds, model substrates are commonly used to increase our understanding of its complex structure. However, few methods have been described for the synthesis of these models. Herein, we describe a new route towards the synthesis of β-O-4 lignin models by intermolecular O-H insertion reactions with simple and stable diazocarbonyls. The benefits of this developed method were shorter reaction times and high yields, as well as mild and environmentally friendly conditions. This journal is

SELECTIVE C-O BOND CLEAVAGE OF OXIDIZED LIGNIN AND LIGNIN-TYPE MATERIALS INTO SIMPLE AROMATIC COMPOUNDS

A method to cleave C-C and C-0 bonds in β-Ο-4 linkages in lignin or lignin sub-units is described. The method includes oxidizing at least a portion of secondary benzylic alcohol groups in β-Ο-4 linkages in the lignin or lignin sub-unit to corresponding ketones and then leaving C-0 or C-C bonds in the oxidized lignin or lignin sub-unit by reacting it with an organic carboxylic acid, a salt of an organic carboxylic acids, and/or an ester of an organic carboxylic acids. The method may utilize a metal or metal-containing reagent or proceed without the metal or metal-containing reagent.

Chemoselective metal-free aerobic alcohol oxidation in lignin

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.