218
MORE et al.
dried over sodium sulfate. Removal of the solvent
Scheme 1.
ArOCOR
afforded products XI XIII (see table).
ArOR
XI XIII
I VIII
Diesters XIV XVII were synthesized as described
above for compounds IX and X using 0.05 mol of
thymol, 0.025 mol of the corresponding acid dihalide,
and 20 ml of 1% aqueous NaOH (see table).
RX
RCOCl
2 min
4 min
OH
REFERENCES
ArOH
X(CH2)nX
ClCO(CH2)nCOCl
n = 1, 2
n = 1 4
2 min
4 min
1. Agarwal, O.P., Chemistry of Organic Natural Prod-
ucts, Meerut (India): GOEL, 1987, vol. 1, p. 408.
XIV XVII
ArO(CH2)nOAr
2. Banthorpe, D.V. and Charlwood, B.V., Chemistry of
Terpenes and Terpenoids, New York, 1972, pp. 337
411.
IX, X
using authentic samples [7 9]. The boiling points
were determined by the open capilary technique and
were not corrected. The reactions were carried out in
a Kenstar OM 9918 C micriwave oven at 2450 MHz.
3. Coats, J.R., Karr, L.L., and Drewas, C.D., Naturally
Occurring Pest Bioregulators, Hedin, P.H., Ed.,
Washington: Am. Chem. Soc., 1991, ACS Symposium
Series, vol. 449, p. 305.
Thymyl ethers I VIII (general procedure).
A mixture of 2.5 mmol of thymol, 10 ml of a 1% so-
lution of NaOH, and 2.5 mmol of the corresponding
alkyl halide was placed in a 100-ml beaker and
irradiated for 4 5 min at a power level of 3. Volatile
alkyl halides were added in small portions after
irradiation for every 1 min. The product was extracted
into benzene or ether (2 20 ml), and the extract was
washed with water and dried over sodium sulfate.
Removal of the solvent afforded thymyl ethers I VIII
(see table).
4. Tsao, R., Lee, S., Rice, P.J., Jensen, C., and
Coats, J.R., Synthesis and Chemistry of Agroche-
micals. Vol. IV, Baker, D.R., Fenyes, J.G., and
Basarab, G.S., Eds., Washington: Am. Chem. Soc.,
1995, ACS Symposium Series, vol. 584, p. 312.
5. Caddick, S., Tetrahedron, 1995, vol. 38, p. 10403.
6. Bose, A., Banik, B., Lavlinskaia, N., and Jayara-
man, M., Chemtech, 1997, vol. 27, pp. 9, 18 24.
7. Kumbhar, P.P. and Dewang, P.M., Pestology, 1999,
vol. 23, p. 27.
8. Kumbhar, P.P., Kapadi, U.R., Hundiwale, D.G.,
Attarde, S.B., Dewang, P.M., and Pawar, N.S., Org.
Prep. Proced. Int., 2000, vol. 32, no. 6, p. 600.
Diethers IX and X were prepared in a similar way
using 0.05 mol of thymol and 0.025 mol of dihalo-
alkane (n = 1, 2) in 20 ml of 1% aqueous NaOH.
9. Kumbhar, P.P. and Dewang, P.M., J. Sci. Ind. Res.,
Thymyl esters XI XIII were synthesized as
described above for ethers I VIII using equimolar
amounts (0.025 mol) of thymol and the corresponding
acid chloride. Volatile acid chlorides were added in
small portions after irradiation for every 1 min. The
organic extract was washed first with a solution of
sodium hydrogen carbonate and then with water and
2001, vol. 60, p. 645.
10. Vogel, A.I., Vogel’s Textbook of Practical Organic
Chemistry, London: Longman Scientific and Tech-
nical, 1989, 5th ed.
11. Kumbhar, P.P., Cand. Sci. Dissertation, Kolhapur,
1993.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 2 2004