83408-07-5Relevant academic research and scientific papers
Synthesis of Naphthol and Its Carbamate Derivatives
Regaila, Hassan A. A.,Gohar, Abd El-Kerim M. N.,El-Khrisy, Ezz El-Din A. M.,Helgemeie, Galal El-Din
, p. 658 - 661 (2007/10/02)
Cyclohex-1-enyl phenyl ketone (Ia) and acetophenone (Ib) on Stobbe condensation with diethyl cyclohex-1-enylsuccinate in the presence of potassium t-butoxide give the corresponding half-esters trans-(Ph/COOC2H5)-2,4-di-(cyclohex-1-enyl)-3-ethoxycarbonyl-4-phenylbut-3-enoic acid (IIa) and trans-(Ph/COOHC2H5)-2-(cyclohex-1-enyl)-3-ethoxycarbonyl-4-methoxy-4-phenylbut-3-enoic acid (IIb).The half-esters (IIa,b) undergo cyclization in the presence CH3COONa/Ac2O to give the acetoxy-esters(IVa,b) which are saponified to give the naphthol derivatives (Va,b).Methylation of Va,b with dimethyl sulphate leads to the formation of the corresponding methoxy esters(VIa,b), which on saponification give the corresponding naphthoic acid derivatives (VIIa,b).Methoxy esters (VIa,b) on heating with Pd/C followed by alkaline hydrolysis afford the fully aromatized 4-methoxy-1,3-diphenyl-2-naphthoic acid (IXa) and 4-methoxy-1-methyl-3-phenyl-2-naphthoic acid (IXb).Also the phenolic acids (Va,b) react with phenyl and methyl isocyanates in boiling benzene in the presence of triethylamine to give the corresponding N-phenyl- and N-methyl-carbamates (VIIIa,b).
