726
G. JOSHI AND S. ADIMURTHY
(ppm) ¼ 137.1 (Quat C), 133.2 (Quat C), 128.9, 128.5, 71.9, 65.8, 15.2. MS (ESI)
(C9H11ClO) ¼ cal. 203.04 [Mþ þ Na], obsd. 203.89.
1-Chloro-4-(propoxymethyl)benzene (Entry 8, Table 2). IR nmax (neat) ¼
1
2962, 2934, 2864, 1488, 1362, 1100, 1015, 810, 482, cmꢁ1. H NMR (CDCl3): d
(ppm) ¼ 7.2 (d, J ¼ 8.5 Hz, 2H), 7.2 (d, J ¼ 8.5 Hz, 2H), 4.4 (s, 2H), 3.4 (s, 2H), 1.6
(q, J ¼ 21.0, 14.0, 7.0 Hz, 2H), 0.9 (t, J ¼ 15.0, 7.5 Hz 3H). 13C NMR (CDCl3): d
(ppm) ¼ 137.4 (Quat C), 133.2 (Quat C), 129.0, 128.6, 72.3, 72.1, 23.1, 10.7. MS
(ESI) (C10H13ClO) ¼ cal. 184.06 [Mþ], obsd. 185.01.
1-Bromo-3-(methoxymethyl)benzene (Entry 9, Table 2). IR nmax (neat) ¼
1
2986, 2927, 2823, 1572, 1470, 1426, 1377, 1198, 1106, 968, 779, 690 cmꢁ1. H NMR
(CDCl3): d (ppm) ¼ 7.4 (s, 1H), 7.4 (d, J ¼ 7.5 Hz, 2 H), 7.2 (d, J ¼ 7.5 Hz, 2H), 4.3 (s,
2H), 7.1 (t, J ¼ 15.0, 7.5 Hz, 2H), 3.2 (s, 3H). 13C NMR (CDCl3): d (ppm) ¼ 140.6
(Quat C), 130.6, 129.9, 127.6, 126.0, 122.5 (Quat C), 73.7, 58.3. MS (ESI)
(C8H9OBr) ¼ cal. 231.9 [Mþ þ MeOH], obsd. 231.77.
1-Bromo-3-(ethoxymethyl)benzene (Entry 10, Table 2). IR nmax (neat) ¼
1
2976, 2928, 2863, 2354, 1572, 1472, 1352, 1201, 1113, 777, 682 cmꢁ1. H NMR
(CDCl3): d (ppm) ¼ 7.4 (s, 1H), 7.3 (d, J ¼ 7.5 Hz, 2H), 7.2 (d, J ¼ 7.0 Hz, 2H), 7.1
(d, J ¼ 7.5 Hz, 2H), 4.3 (s, 2H), 3.4 (q, J ¼ 20.5, 13.5, 6.5 Hz, 2H), 1.1 (t, J ¼ 14.0,
7.0 Hz, 3H). 13C NMR (CDCl3): d (ppm) ¼ 141.0 (Quat C), 130.5, 129.9, 127.6,
126.0, 122.5 (Quat C), 71.9, 66.0, 15.2. MS (ESI) (C9H11OBr) ¼ cal. 246.00
[Mþ þ MeOH], obsd. 246.53.
1-Bromo-3-(propoxymethyl)benzene (Entry 11, Table 2). IR nmax (neat) ¼
1
2963, 2932, 2867, 2335, 1572, 1470, 1357, 1200, 1109, 778, 687 cmꢁ1. H NMR
(CDCl3): d (ppm) ¼ 7.4 (s, 1H), 7.3 (d, J ¼ 7.5 Hz, 2H), 7.2 (d, J ¼ 7.5 Hz, 2H), 7.1
(d, J ¼ 8.0 Hz, 2H), 4.4 (s, 2H), 3.4 (t, J ¼ 13.0, 6.5 Hz, 2H), 1.6 (q, J ¼ 21.5, 14.5,
7.5 Hz, 2H), 0.9 (t, J ¼ 15.0, 7.5 Hz, 3H). 13C NMR (CDCl3): d (ppm) ¼ 141.2 (Quat
C), 134.2, 130.5, 129.9, 127.5, 125.9, 122.5 (Quat C), 72.3, 71.9, 22.9, 10.6. MS (ESI)
(C10H13OBr) ¼ cal. 260.01 [Mþ þ MeOH], obsd. 260.57.
1-(Ethoxymethyl)-4-methoxy-benzene (Entry 12, Table 2). IR nmax
1
(neat) ¼ 2930, 2858, 1612, 1513, 1458, 1248, 1173, 1100, 1035, 817 cmꢁ1. H NMR
(CDCl3): d (ppm) ¼ 7.1 (d, J ¼ 8.5 Hz, 2H), 6.7 (d, J ¼ 8.5 Hz, 2H), 4.3 (s, 2H), 3.6
(s, 3H), 3.4 (d, J ¼ 7.0 Hz, 2H), 1.1 (t, J ¼ 14.0, 7.0 Hz, 3H). 13C NMR (CDCl3): d
(ppm) ¼ 159.1 (Quat C), 129.7 (Quat C), 126.3, 113.7, 72.4, 65.4, 55.2, 15.2. MS
(ESI) (C10H14O2) ¼ cal. 166.09 [Mþ], obsd. 166.79.
1-(Isopropoxymethyl)-4-methoxybenzene (Entry 13, Table 2). IR nmax
1
(neat) ¼ 2967, 2929, 2857, 1613, 1512, 1459, 1248, 1173, 1040, 817, 583 cmꢁ1. H
NMR (CDCl3): d (ppm) ¼ 7.1 (d, J ¼ 8.5 Hz, 2H), 6.7 (d, J ¼ 8.5 Hz, 2H), 4.3 (s,
2H), 3.6 (s, 3H), 3.5 (m, 1H), 1.1 (d, J ¼ 6.0 Hz, 6H). 13C NMR (CDCl3): d
(ppm) ¼ 159.0 (Quat C), 129.7 (Quat C), 129.1, 113.7, 70.6, 69.7, 55.2, 22.1. MS
(ESI) (C10H14O2) ¼ cal. 180.11[Mþ], obsd. 180.69.
1,4-Bis(methoxymethyl)benzene (Entry 1, Table 3). IR nmax (neat) ¼
2976, 2930, 2865, 1450, 1377, 1101, 1018, 849, 812 cmꢁ1 1H NMR (CDCl3): d
.