3000
R. N. Ram, N. K. Meher / Tetrahedron 58 &2002) 2997±3001
1H). 13C NMR 3CDCl3): d 3ppm) 17.96, 38.75, 68.67,
126.77, 127.17, 128.50, 142.68, 160.91.
4.7 Hz), 4.49 3t, 2H, J4.7 Hz), 4.78 3s, 1H, D2O-exchange-
able), 6.75±6.82 3m, 4H), 8.12 3s, 1H). 13C NMR 3CDCl3): d
3ppm) 62.47, 66.42, 115.92, 116.11, 150.14, 152.19, 161.25.
Analysis: Found C, 59.62; H, 5.69%, C9H10O4 requires C,
59.34; H, 5.53%. MS 3m/z): 182 3M1, 12%), 110
3p-HOC6H4OH1, 25%), 73 3CH2CH2OCHO1, 100%).
1.2.7. 2-Benzoyloxyethyl formate 8).32 Colourless liquid.
IR 3neat): nmax 3cm21) 2952, 1724, 1452, 1277, 1175, 1110.
1H NMR 3CDCl3): d 3ppm) 4.44 3d, 4H, J4.8 Hz), 7.33±
7.38 3m, 2H), 7.46±7.50 3m, 1H), 7.94±8.02 3m, 3H). 13C
NMR 3CDCl3): d 3ppm) 61.52, 62.32, 128.35, 129.62,
133.15, 160.57, 166.19.
1.2.14. 2- 3-Hydroxyphenoxy)ethyl formate 21). Colour-
less crystals 3pentane1ether), mp 67±688C. IR 3KBr): nmax
3cm21) 3323 3m, br), 2961, 2941, 1686, 1594, 1493, 1451,
1
1223, 1179, 1151. H NMR 3CDCl3): d 3ppm) 4.17 3t, 2H,
1.2.8. 3- Methoxycarbonyl)benzyl formate 9). Colour-
less crystals 3pentane), mp 492508C. IR 3KBr): nmax
3cm21) 2954, 1724, 1449, 1436, 1290, 1207,1159, 1109,
J4.6 Hz), 4.51 3t, 2H, J4.6 Hz), 5.32 3s, 1H, D2O-
exchangeable), 6.42±6.50 3m, 3H), 7.13 3t, 1H, J
8.1 Hz), 8.12 3s, 1H). 13C NMR 3CDCl3): d 3ppm) 62.33,
65.44, 102.22, 106.68, 108.52, 130.18, 156.83, 159.39,
161.42. Analysis: Found C, 59.24; H, 5.67%, C9H10O4
requires C, 59.34; H, 5.53%. MS 3m/z): 182 3M1, 16%),
110 3m-HOC6H4OH1 16%), 73 3CH2CH2OCHO1, 100%).
1
750. H NMR 3CDCl3): d 3ppm) 3.93 3s, 3H), 5.25 3s,
2H), 7.46 3t, 1H, J7.6 Hz), 7.57 3d, 1H, J7.6 Hz), 8.02
3d, 1H, J7.8 Hz), 8.05 3s, 1H), 8.15 3s, 1H). 13C NMR
3CDCl3): d 3ppm) 51.95, 64.70, 128.53, 129.03, 129.34,
130.40, 132.36, 135.52, 160.39, 166.33. Analysis: Found
C, 62.14; H, 5.22%, C10H10O4 requires C, 61.85; H,
5.19%. MS 3m/z): 194 3M1, 63%), 164 3M12HCHO),
163 3M12OCH3, 59%), 149 343%), 133 360%), 107, 89
3100%), 77, 63, 51.
Acknowledgements
We are grateful tothe DST and the CSIR, New Delhi for
®nancial assistance.
1.2.9. Cyclododecanyl formate 12).19 Colourless liquid.
1
IR 3neat): nmax 3cm21) 2933, 2864, 1724, 1471, 1183. H
NMR 3CDCl3): d 3ppm) 1.35±1.80 3m, 22H), 5.14 3m, 1H),
8.05 3s, 1H). 13C NMR 3CDCl3): d 3ppm) 20.67, 23.02,
23.18, 23.63, 23.85, 28.91, 71.87, 160.55.
References
1. 3a) Green, T. W.; Wuts, P. G. M. Protective Groups in
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Protection of Alcoholic Hydroxyl Groups and Glycols
Systems, McOmie, J. F. W., Ed.; Plenum: London, 1976;
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1.2.10. 9-Fluorenyl formate 14). Colourless crystals
3pentane), mp 74±768C. IR 3KBr): nmax 3cm21) 3005,
2926, 1715, 1453, 1310, 1155, 926, 757, 735. H NMR
1
3CDCl3): d 3ppm) 6.89 3s, 1H), 7.30 3t, 2H, J7.4 Hz),
7.42 3t, 2H, J7.4 Hz), 7.55 3d, 2H, J7.4 Hz), 7.67 3d,
2H, J7.5 Hz), 8.39 3s, 1H). 13C NMR 3CDCl3): d 3ppm)
74.45, 119.90, 125.72, 127.70, 129.45, 140.88, 141.21,
161.40. Analysis: Found C, 79.49; H, 4.17%, C14H10O2
requires C, 79.98, H, 4.79%. MS 3m/z): 210 3M1, 64%),
182 3M12CO, 45%), 181 3M12CHO, 58%), 165 3M12
OCHO, 100%).
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3437±3438.
1.2.11. Diphenylmethyl formate 15).34 Colourless liquid.
IR 3neat): nmax 3cm21) 3032, 2929, 1727, 1495, 1454, 1163.
1H NMR 3CDCl3): d 3ppm) 7.00 3s, 1H), 7.29±7.35 3m,
10H), 8.22 3s, 1H). 13C NMR 3CDCl3): d 3ppm) 77.72,
128.52, 129.43, 129.91, 141.07, 161.28.
6. Dymicky, M. Org. Prep. Proced. Int. 1982, 14, 177±181.
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1.2.12. 2- 4-Hydroxyphenyl)ethyl formate 19). Colour-
less crystals 3pentane1ether), mp 468C. IR 3KBr): nmax
3cm21) 3344, 2958, 1686, 1517, 1219 IR 3Neat): nmax
8. Olah, G. A.; Vankar, Y. D.; Arvanaghi, M.; Sommer, J.
Angew. Chem., Int. Ed. Engl. 1979, 18, 614.
1
3cm21) 3403 3m, br), 1717, 1614, 1516, 1220, 1172. H
NMR 3CDCl3): d 3ppm) 2.90 3t, 2H, J6.9 Hz), 4.34 3t,
2H, J6.9 Hz), 5.55 3bs, 1H, D2O-exchangeable), 6.78 3d,
2H, J8.1 Hz), 7.08 3d, 2H, J8.1 Hz), 8.04 3s, 1H). 13C
NMR 3CDCl3): d 3ppm) 33.90, 64.86, 115.44, 129.01,
129.92, 154.54, 161.56. Analysis: Found C, 64.51; H,
5.97%, C9H10O3 requires C, 65.05, H, 6.06%. MS 3m/z):
1663M1, 10%), 1203M12HCOOH, 100%), 107, 77.
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1.2.13. 2- 4-Hydroxyphenoxy)ethyl formate 20). Colour-
less crystals 3pentane1ether), mp 71±728C. IR 3KBr): nmax
3cm21) 3400 3s, br) 2959, 2928, 1717, 1697, 1511, 1217,
1179, 1080. H NMR 3CDCl3): d 3ppm) 4.14 3t, 2H, J
13. Hagiwara, H.; Morohashi, K.; Sakai, H.; Suzuki, T.; Ando, M.
Tetrahedron 1998, 54, 5845±5852.
14. Habibi, M. H.; Tangestaninejad, S.; Mirkhani, V.; Yadollahi,
B. Tetrahedron 2001, 57, 8333±8337.
1