376
Y.-D. Park et al.
2
180, 1040, 1000 cm . Anal. Calcd for C H O : C, 75.57; H, 5.55. Found
1
1
C, 75.68; H, 5.61.
1
6 14 3
[
22]
Benzoic anhydride (2b). Yellow solid, mp 40–418C [Lit.
mp
1
4
8
0–41 8C]; H NMR (CDCl ) d: 7.50–7.54 (m, 4H), 7.66–7.69 (m, 2H),
3
1
.16–8.25 (m, 4H); C NMR (CDCl ) d: 128.9, 129.0, 130.6, 134.5, 162.4;
3
3
2
1
IR (KBr): 3065, 1785, 1725, 1598, 1451, 1213, 1039, 720 cm . Anal.
Calcd for C H O : C, 74.33; H, 4.46. Found C, 74.41; H, 4.50.
1
4 10 3
4
-Methoxybenzoic anhydride (2c). Light yellow solid, mp 89–908C
[22]
1
[Lit.
mp 89–908C]; H NMR (CDCl ) d: 3.89 (s, 6H), 6.98 (m, 4H),
3
1
.09 (m, 4H); C NMR (CDCl ) d: 55.6, 114.2, 121.3, 132.8, 162.3, 164.6;
3
8
IR (KBr): 3010, 2990, 1790, 1720, 1620, 1300, 1220, 1180, 1040,
3
2
1
1000 cm . Anal. Calcd for C H O : C, 67.13; H, 4.93. Found C, 67.20;
16 14 5
H, 5.01.
4
H NMR (CDCl ) d: 7.50–7.52 (m, 4H), 8.06–8.08 (m, 4H); C NMR
-Chlorobenzoic anhydride (2d). Yellow solid, mp 184–1858C;
1
13
3
(
CDCl ) d: 127.1, 129.4, 131.9, 141.4, 161.3; IR (KBr): 3010, 1800, 1720,
3
2
600, 1500, 1400, 1220, 1180, 1060, 1000 cm ; Anal. Calcd for
1
1
C H O Cl : C, 56.98; H, 2.73; Cl, 24.03. Found C, 57.02; H, 2.81; Cl, 24.12.
1
4
8
3
2
4
-Phenylbenzoic anhydride (2e). Light yellow solid, mp 137–1398C
[22]
1
[
Lit.
mp 138–1408C]; H NMR (CDCl ) d: 7.43 (d, 2H, J ¼ 7.5 Hz),
3
7
8
1
1
6
.49 (t, 4H, J ¼ 7.5 Hz), 7.65 (d, 4H, J ¼ 7.5 Hz), 7.75 (d, 4H, J ¼ 8 Hz),
1
3
.24 (d, 4H, J ¼ 8.5 Hz); C NMR (CDCl ) d: 127.4, 127.6, 127.7, 128.6,
3
29.1, 131.2, 139.6, 147.4, 162.4; IR (KBr): 3010, 1770, 1730, 1600, 1500,
2
400, 1300, 1220, 1170, 1050, 980 cm ; Anal. Calcd for C H O : C,
1
1
6 14 5
7.13; H, 4.93. Found C, 67.20; H, 5.01.
,4-Dichlorobenzoic anhydride (2f). Light yellow solid, mp 120–
2
1
1
218C; H NMR (CDCl ) d: 7.38 (dd, 2H, J ¼ 10.0 Hz), 7.56 (d, 2H,
3
1
3
J ¼ 5.0 Hz), 7.97 (d, 2H, J ¼ 10.0 Hz); C NMR (CDCl ) d: 126.2, 127.5,
3
1
1
31.5, 133.6, 136.3, 140.5, 159.4; IR (KBr): 3010, 1800, 1740, 1600, 1560,
2
480, 1380, 1300, 1200, 1140, 1070, 1020 cm ; Anal. Calcd for
1
C H Cl O : C, 46.19; H,1.66; Cl, 38.96. Found C, 46.23; H, 1.71; Cl, 39.00.
1
4
6
4 3
Furan-2-carboxylic anhydride (2g). Light yellow solid, mp 68–698C;
1
H NMR (CDCl ) d: 6.61–6.62 (m, 2H), 7.42 (d, 2H, J ¼ 2.5 Hz), 7.71
3
1
3
(
d, 2H, J ¼ 1.0 Hz); C NMR (CDCl ) d: 112.9, 121.9, 143.2, 148.8,
3
1
53.1; IR (KBr): 3150, 1800, 1740, 1680, 1580, 1480, 1400, 1320, 1280,
2
1
1
Found C, 58.36; H, 2.98.
180, 1100, 1060, 1020 cm ; Anal. Calcd for C H O : C, 58.26; H, 2.93.
10 6 5
1
Hexanoic anhydride (2h). Colorless oil; H NMR (CDCl ) d: 0.88–0.92
m, 6H), 1.33–1.35 (m, 8H), 1.62–1.67 (m, 4H), 2.35 (t, 4H, J ¼ 7.8); C
NMR (CDCl ) d: 13.9, 22.3, 24.4, 31.2, 33.9, 179.9; IR (KBr): 2900, 2850,
3
1
3
(
3
2
1
1
H,10.35. Found C, 67.26; H, 10.35.
820, 1750, 1480, 1420, 1050 cm ; Anal. Calcd for C H O : C, 67.26;
12 22 3
1
Acetic anhydride (2i). Colorless oil; H NMR (CDCl ) d: 2.20 (s, 6H);
3
1
3
C NMR (CDCl ) d: 16.8, 166.0; IR (KBr): 2900, 2850, 1780, 1690, 1480,
3