Jozef Hodyl PhD Thesis - Theses - Flinders University

C, -CH 2 - CH 2 OSO 2 ); 68.11 (1 C, -CH 2 -OSO 2 ); 61.08 (1 C, CH 2 -OH); 21.21 (1 C, -CH 3 ).1-[2-(2-hydroxyethoxy)ethoxy]-4-benzyloxybenzene•0.5H 2 , 6666The named compound was synthesised by a procedure modified from Amabilinoand co-workers. 244 A solution of 4-(benzyloxy)phenol, 68, (2.34 g, 11.70 mmol),dissolved in anhydrous DMF (10 cm 3 ) was added slowly over 10 min. to a stirringsuspension of finely ground anhydrous K 2 CO 3 , (4.04 g, 29.30 mmol), in anhydrousDMF (5 cm 3 ). The mixture was stirred at 80 o C for 1 h in an atmosphere of nitrogen.A solution of the tosylate 64 (3.10 g, 11.90 mmol), dissolved in dry DMF (10 cm 3 )was then added dropwise and stirred for 4 days at 80 o C. The mixture was dilutedwith water, (1 x 200 cm 3 ), and extracted with CH 2 Cl 2 , (5 x 100 cm 3 ). The CH 2 Cl 2extracts were washed with KHSO 4 , (1M, 3 x 100 cm 3 ), brine, (3 x 100 cm 3 ), andwater, (3 x 100 cm 3 ), and dried over MgSO 4 .The solvent was removed in vacuo toyield a brown oil which was purified by column chromatography over silica (eluent40% EtOAc/DCM, rf: 0.35 ), and concentrated in vacuo to obtain 66 as an off-whiteoil which solidified overnight into a white waxy solid, (2.6 g, 76%). 1 H NMR(CDCl 3 ): δ 7.38-7.30 (5 H, m,, Bn-H); 6.92-6.85 (4 H, m, Ar-H); 5.01 (2 H, s, Bn-CH 2 -); 4.10-3.84 (2 H, m, -OCH 2 ); 3.78-3.76 (2H, m, -OCH 2 ); 3.76-3.66 (4 H, m, -OCH 2 ); 2.10 (1 H, br s, -OH). 13 C NMR (CDCl 3 ): δ 153.19 (1 C, Ar, para); 152.94(1 C, Ar, ipso); 137.18 (1 C, Bn, ipso);128.48 (2 C, Bn, meta); 127.83 (1 C, Bn,127