89102-11-4Relevant academic research and scientific papers
Homologation d'hydroxymethyl anthraquinones
Gesson, Jean-Pierre,Renoux, Brigitte
, p. 901 - 904 (2007/10/02)
2-Hydroxymethyl anthraquinones (Aq-CH2OH) bearing at least one phenolic group in the ortho position (C-1) afford in presence of triethyl orthoacetate and of a catalytic amount of p-toluenesulfonic acid, homologous esters of type Aq-CH2-CH2COOEt. 2-Hydroxy benzyl alcohol behaves similarly while 4-hydroxy benzyl alcohol gives only the corresponding benzyl ether.In situ, formation of both a protonated quinone methide from Aq-CH2OH and of diethoxy-1,1 ethene from triethyl orthoacetate followed by concerted or step-wise condensation accounts for the formation of the observed esters Aq-CH2-CH2COOEt.
