The reaction of 1-(benzyloxy)-4-(hexyloxy)benzene (12.97 g) as raw material with 5% Pd/C (1.2 g) in 200 mL of 1:1 methanol/ethyl acetate solvent mixture was stirred under hydrogen atmosphere for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete consumption of the raw materials. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst. Subsequently, the solvent in the filtrate was replaced with a 12% ethyl acetate/hexane mixture and filtered through a silica gel pad. Finally, the filtrate was concentrated to give 8.84 g of 4-(hexoxy)phenol. The product was detected by TLC with an Rf value of 0.21 (unfolding agent 10% ethyl acetate/hexane).1H NMR (CDCl3) data were as follows: δ 6.80-6.72 (m, 4H), 3.88 (t, 2H, J = 6.7Hz), 1.79-1.68 (m, 2H), 1.48-1.30 (m, 6H), 0.91-0.86 (m , 3H).
