3632
H. Sharghi, M. Hosseini Sarvari / Tetrahedron 59 (2003) 3627–3633
1075, 800, 750, 701, 665 cm21; m/z 167 (19.9, Mþ), 150
(12.4), 124 (13.5), 106 (40.7),78 (100), 51 (65.6%).
62.69; H, 6.58. C11H14O4 requires C, 62.85; H, 6.71%]; dH
(CDCl3) 3.72 (m, 4H, –OCH2CH2OH), 3.85 (t, 2H,
J¼2.50 Hz, PhCO2CH2CH2O–), 4.50 (t, 2H, J¼2.75 Hz,
PhCO2CH2CH2O–), 7.41–7.59 (m, 3H, Ar-H), 8.06 (d, 2H,
J¼5.00 Hz, Ar-H); dC (CDCl3): 63.20, 64.91, 66.18, 68.65,
130.53, 131.82, 132.07, 135.29, 169.14; nmax (neat): 3416,
2916, 1717, 1600, 1449, 1320, 1274, 1200, 1165, 1130,
1066, 1033, 890 cm21; m/z 210 (1.1, Mþ), 149 (19.7), 105
(100), 77 (31.6), 45 (32.5%).
3.2.8. 2-Hydroxyethyl levulinate (23). [Found: C, 52.3; H,
7.31 C7H12O4 requires C, 52.49; H, 7.55%]; dH (CDCl3) d
2.19 (s, 3H, CH3CO–), 2.61 (t, 2H, J¼5.00 Hz, –CH3-
COCH2CH2CO2–), 2.77 (t, 2H, J¼5.50 Hz, CH3COCH2-
CH2CO2–), 3.77 (t, 2H, J¼1.50 Hz, –CH2OH), 4.25 (t, 2H,
J¼8.00 Hz, –CO2CH2CH2OH); dC (CDCl3): 28.10, 30.170,
38.04, 62.31, 67.58, 172.73, 206.92; nmax (neat) 3450, 1740,
1415, 1410, 1350, 1175, 1075, 1015, 975, 920, 804 cm21
;
3.2.15. Triethyleneglycol monobenzoate (36). dH (CDCl3)
3.62–3.97 (m, 10H, PhCO2CH2(CH2OCH2)2CH2OH), 4.46
(t, 2H, J¼2.90 Hz, PhCO2CH2(CH2OCH2)2CH2OH), 7.39–
7.75 (m, 3H, Ar-H), 8.05 (d, 2H, J¼7.25 Hz, Ar-H); dC
(CDCl3): 61.38, 64.49, 69.58, 70.38, 72.75, 128.74, 130.05,
130.37, 133.48, 166.98; nmax (neat) 3416, 2916, 1717, 1600,
1592, 1440, 1260, 1200, 1115, 1043, 860 cm21; m/z 254
(0.8, Mþ), 149 (20), 105 (100), 77 (29.5), 45 (32%).
m/z 160 (1.6, Mþ), 143 (64.4), 123 (15.1), 99 (100), 43
(63.3%).
3.2.9. 2-Hydroxyethyl stearate (24). dH (CCl4) 0.88 (t, 3H,
J¼6.20 Hz, CH3–), 1.26–1.58 (m, 30H, CH3(CH2)15CH2-
CO2–), 2.30 (t, 2H, J¼6.25 Hz, CH3(CH2)15CH2CO2–),
3.70 (t, 2H, J¼4.86 Hz, –CH2OH), 4.12 (t, 2H, –CO2CH2-
CH2OH); dC (CCl4): 16.64, 25.12, 27.225, 31.58–34.35,
36.31, 63.19, 67.99, 175.27; nmax (KBr) 3400, 2920, 2860,
1740, 1518, 1185, 720 cm21; m/z 328 (0.7, Mþ), 104 (14.6),
69 (17.8), 43 (100), 41 (72.9%).
3.2.16. Tetraethyleneglycol monobenzoate (37). dH
(CDCl3) 3.54–4.70 (m, 16H, –O(CH2CH2O)3CH2CH2OH),
7.31–7.47 (m, 3H, Ar-H), 7.95 (d, 2H, J¼7.00 Hz, Ar-H);
dC (CDCl3): 61.44, 63.17, 63.99, 66.91, 128.77, 130.07,
130.41, 133.54, 166.89; nmax (neat) 3416, 2916, 1717, 1600,
1592, 1440, 1315, 1260, 1200, 1115, 1043, 860 cm21; m/z
298 (0.2, Mþ), 149 (56.2), 105 (100), 77 (24.6), 45 (23.9%).
3.2.10. 2-Hydroxyethyl 11-bromoundecanoate (25).
[Found: C, 50.21; H, 7.95. C13H25BrO3 requires C, 50.49;
H, 8.15%]; dH (CDCl3) 1.29–1.63 (m, 16H, BrCH2(CH2)8-
CH2CO2–), 2.33 (t, 2H, J¼7.25 Hz, BrCH2(CH2)8CH2-
CO2–), 3.40 (t, 2H, J¼6.72 Hz, BrCH2(CH2)8CH2CO2–),
3.83 (t, 2H, J¼4.47 Hz, –CH2OH), 4.22 (t, 2H, J¼4.37 Hz,
–OCH2CH2OH); dC (CDCl3): 25.02, 25.13–29.61, 33.09,
34.23, 61.09, 66.03, 173.65; nmax (KBr) 3416, 2916, 2840,
1750, 1460, 1200 cm21; m/z 309 (4.7, Mþ), 291 (27.8), 79
(12.1), 45 (100), 43 (21.1%).
3.2.17. Pentaethyleneglycol monobenzoate (38). [Found:
C, 59.46; H, 7.50. C17H26O7 requires C, 59.64; H, 7.65%];
dH (CDCl3) 3.91–4.83 (m, 20H, –O(CH2CH2O)4CH2CH2-
OH), 7.70–7.89 (m, 3H, Ar-H), 8.39 (d, 2H, J¼7.15 Hz, Ar-
H); dC (CDCl3): 61.58, 67.56, 128.78, 128.91, 130.14,
133.69, 167.37; nmax (neat) 3445, 2970, 1726, 1610, 1593,
1500, 1460, 1380, 1325, 1285, 1185, 1130, 1078, 1035,
720 cm21; m/z 342 (Mþ), 149 (95), 105 (100), 77 (18.8), 45
(11.1%).
3.2.11. 2-Hydroxyethyl cyclohexanoate (26). dH (CDCl3)
1.23–1.89 (m, 10H, C6H10), 3.79 (t, 2H, J¼3.00 Hz,
–CH2OH), 4.18 (t, 2H, J¼2.92 Hz, –OCH2CH2OH); dC
(CDCl3): 25.59, 25.93, 29.17, 43.19, 60.84, 65.85, 176.34;
3.2.18. Hexaethyleneglycol monobenzoate (39). dH
(CDCl3) 3.49–4.63 (m, 20H, –O(CH2CH2O)5CH2CH2OH),
7.36–7.69 (m, 3H, Ar-H), 8.03 (d, 2H, J¼6.87 Hz, Ar-H);
dC (CDCl3): 61.24, 66.92, 128.74, 128.89, 130.02, 133.66,
167.34; nmax (neat) 3440, 2950, 1720, 1605, 1585, 1452,
1275, 1178, 1125, 1070, 1029, 928, 710 cm21; m/z 386
(Mþ), 167 (20), 149 (84.4), 123 (17), 105 (100), 77 (20.8),
45 (22.4%).
n
max (neat) 3440, 2940, 2870, 1740, 1455, 1320, 1255, 1200,
1180, 1140, 1050 cm21; m/z 172 (3.0, Mþ), 155 (100), 129
(10.0), 11 (40.8), 83 (39.9), 55 (30.9%).
3.2.12. 8-Hydroxyoctyl benzoate (31). [Found: C, 71.74;
H, 8.64. C15H22O3 requires C, 71.97; H, 8.86%]; dH
(CDCl3): 1.26–1.79 (m, 12H, PhCO2CH2(CH2)6CH2OH),
3.63 (t, 2H, J¼6.40 Hz, –CH2OH), 4.29 (t, 2H, J¼6.50 Hz,
PhCO2CH2(CH2)6CH2OH), 7.29–7.55 (m, 3H, Ar-H), 8.05
(d, 2H, J¼7.25 Hz, Ar-H); dC (CDCl3): 26.06, 26.49, 29.06,
29.68, 33.03, 63.19, 65.49, 128.7, 129.59, 130.30, 133.22,
167.14; nmax (neat) 3425, 2941, 2904, 1724, 1604, 1450,
1284, 1120, 715 cm21; m/z 250 (1.2, Mþ), 123 (58.8), 105
(100), 77 (40.8), 41 (43.8%).
3.2.19. 2-Aminoethyl benzoate (40). To a mixture of
MeSO3H (1.0 mL, 1.5£10 mmol) and Al2O3 (0.27 g,
3.0 mmol) were added benzoic acid (1a) (0.12 g,
1.0 mmol) and 2-amino-1-ethanol (12) (0.06 mL,
1.0 mmol), respectively. The mixture was stirred and heated
in an oil bath at 808C for an appropriate time. Then the
mixture was poured into a saturated solution of sodium
bicarbonate and extracted two times with ethyl acetate
(20 mL). The organic layer was dried over CaCl2 and
evaporated in vacuo to give the products.
3.2.13. 8-(Benzoyloxy)octyl benzoate (32). dH (CDCl3)
1.18–2.08 (m, 12H, PhCO2CH2(CH2)6CH2–), 4.24 (t, 4H,
J¼5.00 Hz, PhCO2CH2(CH2)6CH2–), 7.18–7.49 (m, 6H,
Ar-H), 7.97 (d, 4H, J¼7.70 Hz, Ar-H); dC (CDCl3): 26.38,
29.09, 29.57, 65.44, 128.71, 129.92, 130.90, 133.20, 167.08;
nmax (KBr) 2933, 2891, 1718, 1600, 1475, 1315, 1280,
1114, 717 cm21; m/z 354 (6.7, Mþ), 329 (3.8), 123 (58.8),
105 (100).
[Found: C, 65.27; H, 6.52. C9H11NO2 requires C, 65.44; H,
6.71%]; dH (CDCl3) 3.53 (t, 2H, J¼2.50 Hz, –OCH2CH2-
NH2), 3.73 (t, 2H, J¼3.00 Hz, –OCH2CH2NH2), 4.67 (s,
2H, –NH2), 7.31 (m, 3H, Ar-H), 7.74 (d, 2H, J¼7.35 Hz,
Ar-H); dC (CDCl3): 43.19, 61.98, 127.44, 128.87, 130.09,
133.69, 169.19; nmax (neat) 3357, 3074, 2948, 1724, 1652,
3.2.14. Diethyleneglycol monobenzoate (35). [Found: C,