A. K. Chakraborti et al. / Tetrahedron 59 (2003) 7661–7668
7667
NMR d 20.3, 20.6, 119.8, 125.3, 126.1, 135.6, 145.9, 153.4,
168.3; EIMS (m/z) 195 (Mþ), 43 (100).
1.4.11. 2,4-Diacetoxy acetophenone (Table 4, entry 22).
1
Oil. IR (neat) 1770, 1688 cm21; H NMR d 2.31 (s, 3H),
2.34 (s, 3H), 2.54 (s, 3H), 6.96 (d, J¼2.1 Hz, 1H), 7.10 (dd,
J¼2.1, 8.5 Hz, 1H), 7.84 (d, J¼8.5 Hz, 1H); 13C NMR d
21.1, 29.3, 117.3, 119.1, 128.0, 131.3, 150.0, 153.9, 168.3,
169.0, 196.3; EIMS (m/z) 236 (Mþ), 43 (100). CHN Anal.
calcd for C12H12O5: C 61.02, H 5.08. Found: C 61.15, H
5.05.
1.4.3. 3-Acetylphenylacetate (Table 4, entry 12).52 IR
1
(neat) 1767, 1687 cm21; H NMR d 2.33 (s, 3H), 2.60 (s,
3H), 7.68 (s, 1H), 7.31 (d, J¼8.0 Hz, 1H), 7.45–7.48 (m,
1H), 7.83 (d, J¼8.0 Hz, 1H); 13C NMR d 20.6, 26.3, 121.1,
125.4, 126.1, 129.3, 138.1, 150.6, 168.9, 196.8; EIMS (m/z)
178 (Mþ), 121 (100).
1.4.12. 5-Methyl-2-nitrophenylacetate (Table 5, entry 5).
Oil. IR (neat) 1775 cm21; H NMR d 2.37 (s, 3H), 2.44
1
1.4.4. 4-Methoxybenzylacetate (Table 6, entry 3).40 IR
1
(neat) 1720 cm21; H NMR d 2.05 (s, 3H), 3.78 (s, 3H),
(s, 3H), 7.03 (s, 1H), 7.18 (d, J¼8.2 Hz, 1H), 8.02 (d, J¼
8.2 Hz, 1H); 13C NMR d 20.3, 20.9, 125.2, 125.3, 127.0,
138.9, 143.7, 146.6, 168.4; EIMS (m/z) 195 (Mþ), 43 (100).
CHN Anal. calcd for C9H9NO4: C 55.38, H 4.6, N 7.17.
Found: C 54.99, H 4.54, 6, N 7.12.
5.02 (s, 2H), 6.87 (d, J¼8 Hz, 2H), 7.27 (d, J¼8 Hz, 2H);
13C NMR d 20.9, 55.1, 64.7, 113.6, 129.3, 130.3, 159.0,
170.9; EIMS 180 (Mþ), 121 (100).
1.4.5. 4-Chloro-3-methyl-phenylacetate (Table 4, entry
10).39 IR (neat) 1764 cm21; 1H NMR d 2.28 (s, 3H), 2.36 (s,
3H), 6.97 (s, 1H), 6.87 (d, J¼8.5 Hz, 1H), 7.32 (d, J¼
8.5 Hz, 1H); 13C NMR d 20.1, 20.9, 120.2, 123.8, 129.6,
131.3, 137.3, 148.9, 169.3; EIMS (m/z) 184 (Mþ), 142 (100).
1.4.13. 2-Mercaptothiazolylacetate (Table 4, entry 28).
1
Oil. IR (neat) 1694 cm21; H NMR d 2.76 (s, 3H), 3.35 (t,
J¼7.55 Hz, 2H), 4.59 (t, J¼7.53 Hz, 2H); 13C NMR d 26.6,
27.9, 55.3, 87.9, 201.6; EIMS (m/z) 152 (Mþ), 43 (100).
CHN Anal. calcd for C5H7NOS2: C 37.2, H 4.34, N 8.69, S
39.6. Found: C 37.2, H 4.31, N 8.54, S 39.6.
1.4.6. 1,3-diacetoxybutane (Table 6, entry 22).10b IR
(neat) 1740 cm21; 1H NMR d 1.25 (d, J¼6.2 Hz, 3H), 1.90
(m, 2H), 2.1 (s, 6H), 4.11 (t, J¼6.3 Hz, 2H), 5.01 (q, J¼
6.3 Hz, 1H); 13C NMR d 19.9, 20.7, 21.1, 34.6, 60.6, 67.7,
170.4, 170.8.
1.4.14. Isomenthyl acetate (Table 6, entry 10). Oil.
1
[a]D25¼þ30 (c¼10, C6H6); IR (neat) 1708 cm21; H NMR
d 0.85 (d, 3H, J¼7 Hz), 0.93 (m, 6H), 1.24–1.87 (m, 9H),
2.03 (s, 3H), 4.99–5.05 (m, 1H); 13C NMR d 18.9, 20.4,
20.8, 21.4, 26.2, 27.5, 29.9, 35.8, 45.8, 71.6, 170.6; EIMS
(m/z) 138 (M257), 43 (100). CHN Anal. calcd for
C12H22O2: C 72.73, H 11.11. Found: C 72.67, H 11.02.
The following acylated products were not reported in the
literature.
1.4.7. 2,3,6-Trimethylphenyl acetate (Table 4, entry 6).
Oil. IR (neat) 1761 cm21; 1H NMR d 2.04 (s, 3H), 2.16 (s,
3H), 2.23 (s, 3H), 2.31 (s, 3H), 6.93 (s, 2H); 13C NMR d
12.4, 16.1, 19.6, 20.3, 127.1, 127.5, 128.4, 135.4, 147.9,
168.8; EIMS (m/z) 178 (Mþ), 135 (100). CHN Anal. calcd
for C11H14O2: C 74.15, H 7.86. Found: C 74.45, H 7.66.
1.4.15. Diacetoxy diethyl tartarate (Table 6, entry 23).
White crystal, mp 65–688C; [a]2D5¼24.8 (c¼1, DCM),
1
24.0 (c¼1, EtOH); IR (KBr) 1759 cm21; H NMR d 1.27
(t, J¼7 Hz, 6H), 2.17 (s, 6H), 4.25 (q, J¼7 Hz, 4H), 5.71 (s,
2H); 13C NMR d 14.0, 20.2, 62.2, 70.5, 165.7, 169.5. CHN
Anal. calcd for C12H18O8: C 49.66, H 6.21. Found: C 49.50,
H 6.53.
1.4.8. 2-Acetylphenyl acetate (Table 4, entry 13). Light
yellow crystal, mp 89–928C; IR (KBr) 1756, 1684 cm21
;
1H NMR d 2.32 (s, 3H), 2.52 (s, 3H), 7.10 (d, J¼8.0 Hz,
1H), 7.28 (t, J¼7.6 Hz, 1H), 7.50 (t, J¼7.7 Hz, 1H), 7.78 (d,
J¼7.8 Hz, 1H); 13C NMR d 20.9, 29.1, 123.6, 125.8, 130.1,
130.5, 133.2, 148.8, 169.2, 197.3; EIMS (m/z) 178 (Mþ), 43
(100). CHN Anal. calcd for C10H10O3: C 67.42, H 5.62.
Found: C 67.75, H 5.50.
1.4.16. 2,3,6-Trimethylphenyl-benzoate (Table 7, entry
1
6). White crystal, mp 55–588C; IR (KBr) 1734 cm21; H
NMR d 2.08 (s, 3H), 2.15 (s, 3H), 2.27 (s, 3H), 6.99 (s, 2H),
7.50 (t, J¼7.5 Hz, 2H), 7.63 (t, J¼7.4 Hz, 1H), 8.25 (d,
J¼7.2 Hz, 2H); 13C NMR d 12.6, 16.3, 19.8, 127.2, 127.4,
127.64, 128.5, 129.3, 130.1, 133.5, 135.6, 148.1, 164.5;
EIMS (m/z) 240 (Mþ), 105 (100). CHN Anal. calcd for
C16H16O2: C 80.00, H 6.67. Found: C 80.22, H 6.52.
1.4.9. Ethyl-4-acetoxybenzoate (Table 4, entry 15). Oil.
1
IR (neat) 1762, 1717 cm21; H NMR d 1.38 (t, J¼7.1 Hz,
3H), 2.30 (s, 3H), 4.35 (q, J¼7.1 Hz, 2H), 7.15 (d, J¼
8.6 Hz, 2H), 8.06 (d, J¼8.6 Hz, 2H); 13C NMR d 14.1, 20.9,
61.0, 121.4, 127.8, 131.0, 154.1, 165.8, 168.8; EIMS (m/z)
208 (Mþ), 121 (100). CHN Anal. calcd for C11H12O4: C
63.46, H 5.76. Found: C 63.8, H 6.14.
Acknowledgements
LS and Shivani thank CSIR, New Delhi for award of Senior
and Junior Fellowships, respectively.
1.4.10. n-Propyl-4-acetoxybenzoate (Table 4, entry 16).
1
Oil. IR (neat) 1762, 1717 cm21; H NMR d 1.02 (t, J¼
7.4 Hz, 3H), 1.73–1.89 (m, 2H), 2.3 (s, 3H), 4.26 (t, J¼
7.4 Hz, 2H), 7.18 (d, J¼8.6 Hz, 2H), 8.01 (d, J¼8.6 Hz,
2H); 13C NMR d 10.4, 21.1, 22.0, 66.6, 121.5, 128.0, 131.0,
154.1, 165.9, 168.9; EIMS (m/z) 222 (Mþ), 43 (100). CHN
Anal. calcd for C12H14O4: C 64.86, H 6.36. Found: C 64.8,
H 6.34.
References
1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis; Wiley: New York, 1999. (b) Hanson, J. R.
Protective Groups in Organic Synthesis; Blackwell Science:
Malden, MA, 1999.