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The α-hydroxyl group in lignin model compounds 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol ( 1 ) and 1-(4-hydroxy-3-methoxyphenyl)ethanol ( 3 ), and the α-carbonyl group in 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one ( 5 ) are removed by treatment of the model compounds with trifluoroacetic acid (CF 3 CO OH) and triethylsilane (Et3sih) in methylene chloride. The reaction is highly chemoselective and it tolerates the lignin γ-hydroxyl group, phenol and β-O-4-aryl ether linkage. The α-hydroxyl group in  1  has also been removed with triethylsilane in aqueous trifluoroacetic acid (CF 3 CO OH : H 2 o = 75 : 25).

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A New Approach Towards the Yellowing Inhibition of Mechanical Pulps. Part I: Selective Removal of α-Hydroxyl and α-Carbonyl Groups in Lignin Model Compounds