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3-Benzylphthalide 47
1860; S. L. Shapiro, K. Geiger, J. Youlus and L. Freedman, J. Org.
Chem., 1961, 26, 3580.
3-Benzylidenephthalide 5 was hydrogenated in the presence of
Pd–C (10%) in methanol at room temp. under atmospheric
pressure. After usual work-up, solid product 7 (90%) was
obtained, which was crystallised from diethyl ether–light
petroleum, mp 59–60 ЊC (Found: C, 80.22, H, 5.51. C15H12O2
requires C, 80.33; H, 5.40%); νmax(KBr)/cmϪ1 1752s and 1600w;
λmax(EtOH)/nm 282 (log ε 3.17), 274 (3.18) and 227 (3.96);
δH(300 MHz; CDCl3) 3.16 (1 H, dd, J 14.1 and 6.3, CH2Ar),
3.29 (1 H, dd, J 14.1 and 6.6, CH2Ar), 5.69 (1 H, t, J 6, OCH-
CH2Ar), 7.16–7.32 (6 H, m, ArH), 7.49 (1 H, t, J 7.5, ArH),
7.604 (1 H, td, J 7.5 and 1, ArH) and 7.845 (1 H, d, J 7.8, ArH);
δC(75 MHz; CDCl3) 41.27 (CH2), 81.624, 122.711, 126.100,
126.662, 127.570, 128.954, 129.603, 130.116, 134.126, 135.411,
149.525 and 170.661; δC(75 MHz; CDCl3; DEPT 135) 40.964
(inverted), 81.358, 122.441, 125.800, 127.282, 128.667, 129.327,
129.834 and 133.669.
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Acknowledgements
Thanks are due to the Council of Scientific and Industrial
Research, Government of India, for awarding a Senior
Research Fellowship (M. P.) and a Junior Research Fellowship
(B. N.). Financial support from CSIR [Grant No. 01(1385)/95/
EMR-II to Professor N. G. Kundu] is gratefully acknowledged.
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Paper 7/05450E
Received 28th July 1997
Accepted 25th September 1997
568
J. Chem. Soc., Perkin Trans. 1, 1998