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Acylation of Alkoxy Benzenes
Spectral and Physical Data of the Products
1371
Entry 1. IR (KBr), ꢀ (cmÀ1): 3060 (w), 3000 (w), 2960 (m), 1665 (s),
1600 (s), 1470 (m), 1250 (s), 1020 (s), 830 (s); 1H NMR (CDCl3), ꢁ (ppm):
7.9 (2H, d), 6.9 (2H, d), 3.8 (3H, s), 2.6 (3H, s); m.p. ¼ 35ꢀC (lit.[25] ¼ 37ꢀC),
m.p. of semicarbazone derivative ¼ 195–197ꢀC (lit.[25] ¼ 197–198ꢀC).
Entry 2. IR (KBr), ꢀ (cmÀ1): 3050 (w), 2980 (m), 2910 (w), 1665 (s),
1600 (s), 1475 (m), 1250 (s), 1030 (m), 845 (m); 1H NMR (CDCl3),
ꢁ (ppm): 7.9 (2H, d), 6.9 (2H, d), 4.0 (2H, q), 2.6 (3H, s), 1.3 (3H, t);
m.p. ¼ 34ꢀC (lit.[25] ¼ 36–37ꢀC), m.p. of semicarbazone derivative
178–180ꢀC (lit.[25] ¼ 179–180ꢀC).
Entry 3. IR (neat), ꢀ (cmÀ1): 3060 (w), 2950 (s), 1675 (s), 1600 (s),
1470 (m), 1250(s), 1020 (m), 830 (s);1H NMR(CDCl3), ꢁ(ppm):7.9 (2H, d),
6.8 (2H, d), 4.0 (2H, t), 2.6 (3H, s), 0.9–1.5 (7H, m); m.p. ¼ 23ꢀC
(lit.[26] ¼ 22ꢀC), m.p. of oxime derivative ¼ 83ꢀC (lit.[26] ¼ 86ꢀC).
Entry 4. IR (neat), ꢀ (cmÀ1): 3050 (w), 2950 (s), 1678 (s), 1600 (s),
1
1470 (m), 1250 (s), 1020 (m), 830 (m); H NMR (CDCl3), ꢁ (ppm): 7.8
(2H, d), 6.8 (2H, d), 3.7 (2H, d), 2.6 (3H, s), 2.0 (1H, m), 1.2 (6H, d); m.p.
of oxime derivative ¼ 105–106ꢀC (lit.[27] ¼ 107ꢀC).
Entry 5. IR (neat), ꢀ (cmÀ1): 3050 (w), 2940 (s), 1678 (s), 1600 (s),
1470 (m), 1250 (s), 1030 (m); 1H NMR (CDCl3), ꢁ (ppm): 7.8 (2H, d), 6.8
(2H, d), 4.0 (2H, t), 2.5 (3H, s), 0.8–1.7 (11H, m); m.p. of oxime
derivative ¼ 77ꢀC (lit.[27] ¼ 78ꢀC).
Entry 6. IR (neat), ꢀ (cmÀ1): 3050 (w), 2950 (s), 1675 (s), 1600 (s),
1470 (m), 1255 (s), 1220 (s), 1025 (s), 950 (m), 700 (s); 1H NMR (CDCl3),
ꢁ (ppm): 7.9 (2H, d), 6.9 (2H, d), 3.8 (3H, s), 2.9 (2H, q), 1.2 (3H, t);
m.p. 25–27ꢀC (lit.[25] ¼ 26–27ꢀC), m.p. of semicarbazone derivative ¼
170–172ꢀC (lit.[25] ¼ 171–172ꢀC).
Entry 7. IR (neat), ꢀ (cmÀ1): 3050 (w), 2980 (s), 2910 (s), 1678 (s),
1600 (s), 1475 (w), 1250 (s), 1220 (s), 800 (m); 1H NMR (CDCl3),
ꢁ (ppm): 7.8 (2H, d), 6.9 (2H, d), 4.0 (2H, q), 3.0 (2H, q), 0.9–1.7 (6H, m);
m.p. ¼ 28–30ꢀC (lit.[25] ¼ 29–30ꢀC), m.p. of semicarbazone derivative ¼
182ꢀC (lit.[25] ¼ 181–183ꢀC).
Entry 8. IR (neat), ꢀ (cmÀ1): 3050 (w), 2950 (s), 2910 (s), 1680 (s), 1600 (s),
1
1460 (s), 1250 (s), 1220 (s), 950 (m), 795 (m); H NMR (CDCl3), ꢁ (ppm):
7.8 (2H, d), 6.8 (2H, d), 4.0 (2H, t), 3.0 (2H, q), 0.9–1.8 (10H, m); m.p. ¼
27–29ꢀC (lit.[28] ¼ 28ꢀC), m.p. of oxime derivative ¼ 77ꢀC (lit.[28] ¼ 79ꢀC).
Entry 9. IR (KBr), ꢀ (cmÀ1): 3050 (w), 2950 (s), 2910 (s), 1673 (s),
1600 (s), 1472 (m), 1255 (s), 1230 (s), 1020 (s), 795 (s); 1H NMR (CDCl3),
ꢁ (ppm): 7.9 (2H, d), 6.9 (2H, d), 3.8 (2H, d), 3.0 (2H, q), 2.1 (1H, m),
0.8–1.5 (9H, m); m.p. ¼ 44ꢀC, m.p. of 2,4-dinitrophenylhydrazone
derivative ¼ 155–157ꢀC.