Jozef Hodyl PhD Thesis - Theses - Flinders University

The preparation of this compound was from triethylene glycol (trigol) 62 (6.7 g,44.91 mmol), triethylamine (2.3 g, 22.45 mmol) and tosyl chloride, 63, (2.6 g, 13.47mmol), by the same procedure as for 64 (rf: 0.19). The product 65 was gained as acolourless oil, 3.12 g, 76%. 1 H NMR (CDCl 3 ): δ 7.75 (2 H, d, J = 8.4 Hz, Ar-H;7.29 (2 H, d, J = 8.4 Hz, Ar-H); 4.13-4.10 (2 H, m, -OCH 2 -); 3.67-3.64 (4 H, -OCH 2 -); 3.56-3.50 (6 H, m, -OCH 2 -); 2.60 (1 H, s, -OH); 2.40 (3 H, s, -CH 3 ). 13 C NMR(CDCl 3 ): δ 144.87 (1 C, Ar, para); 132.77 (1 C, Ar, ipso); 129.80 (2 C, Ar, meta);127.89 (2 C, Ar, ortho); 72.33 (1 C, CH 2 -CH 2 OH; 70.68 (1 C, CH 2 -OCH 2 CH 2 OH);70.14 (1 C, -CH 2 -OCH 2 CH 2 OSO2); 69.11 (1 C, -CH 2 -CH 2 OSO 2 ; 68.62 (1 C, CH 2 -OSO 2 ); 61.63 (1 C, CH 2 -OH); 21.58 (1 C, -CH 3 ).1-[2-(2-(2-hydroxyethoxy)ethoxy)ethoxy]-4-benzyloxybenzene, 6767Preparation of this compound was by a method analogous to that used for thepreparation of 66 from 4-(benzyloxy)phenol, 68 (3.25 g, 16.23 mmol), K 2 CO 3 , (5.6g, 40.60 mmol), and 65 (5.01 g, 16.45 mmol), (rf: 0.18), to obtain 67 as an off-whiteoil which solidified overnight into a white, waxy solid (4.6 g, 85%). 1 H NMR(CDCl 3 ): δ 7.44-7.31 (5 H, m, Bn-H); 6.92-6.84 (4 H, m, Ar-H); 5.01 (2 H, s, Bn-CH 2 -); 4.10-4.07 (2 H, m, -OCH 2 -); 3.86-3.82 (2 H, m, -OCH 2 -); 3.75-3.70 (6H, m, -OCH 2 -); 3.63-3.60 (2 H, m, -OCH 2 -); 2.52 (1 H, br s, OH). 13 C NMR (CDCl 3 ): δ153.12 (1 C, Ar, para); 153.01 (1 C, Ar, ipso); 137.21 (1 C, Bn, ipso); 128.46 (2 C,130