SYNTHESIS OF ETHOPHENPROX
1633
134.20 (C_ arom CH2, VIII and IX), 140.48 (C_ arom
CMe2, IX), 141.00 (C_ arom CMe2, VIII), 152.10
(C5aromO, IX), 156.31 (C1 arom O, VIII and IX),
157.41 (C7arom O, VIII). Found, %: C 80.19; H 7.09.
C17H18O2. Calculated, %: C 80.29; H 7.15. m/z:
ether, 10: 1. We obtained 0.28 g (42,5%) of com-
pound I with physical constants consistent with the
published data[1], and 0.07 g (8.5%) of 2-(4-hydr-
oxyphenyl)-2-methylpropyl phenoxybenzyl ether
1
(XVI). H NMR spectrum (XVI), , ppm: 1.30 s
+
254 M+ , 224 (M CH2O ).
[6H, C(C_H3)2], 3.44 s (2H, C_H2CMe2), 4.47 s (2H,
C_H2Ar), 4.80 s (1H, HOAr), 6.71 7.37 m (13H,
C arom H).
p-(1-Chloro-2-methyl-2-propyl)benzenesulfonic
acid sodium salt (X) was prepared by procedure
from [15] in 1.05 g (66%) yield, light gray crystals.
1
REFERENCES
IR spectrum, , cm : 824 (Carom-Cl); 1040, 1240
(RSO3); 1128, 1176, 1376, 1400 (CMe2). UV spec-
trum, MeCN, nm (log ): 223 (3.0234), 252 (0.8304),
268.5(1m.1ax071). 1HNMRspectrum, , ppm [(CD3)2SO]:
1.32 s (6H, CH3), 3.60 s (2H, CH2), 7.35 d (2H,
HCCC, J 7.89), 7.45 d (2H, HCCS, J 7.89). Found,
%: C 44.28; H 4.50; Cl 13.40; Na (ash)8.54;
S 11.54. C10H12ClNaO3S. Calculated, %: C 44.36;
H 4.48; Cl 13.10; Na 8.49; S 11.84.
1. Udagawa, T., Jpn. Pestic. Inf., 1986, no. 48, pp. 23 26;
Chem. Abstr., 1986, vol. 104, 18583e.
2. Promonenkov, V.K., Perlova, T.G., Andreeva, L.N.
et al., Piretroidy. Khimiko-tekhnologicheskie aspekty
(Perithroids. Aspects of Chemistry and Processing),
Moscow: Khimiya, 1992.
3. Japan Patent 58 131 931, 1983; Chem. Abstr., 1983,
vol. 99. 175367w; US Patent 4397864, 1983; Ref. Zh.
Khim., 1984, 11O343P.
4. Organikum, organisch-chemisches Grundpraktikum,
Heidelberg: Johann Ambrosis Barth, 1996.
p-(1-Chloro-2-methyl-2-propyl)aniline (XIV). mp
1
175 C. IR spectrum, , cm : 3328, 3240 (NH2);
1
1390, 1376, 1165, 1136 (CMe2); 848 (CCl). HNMR
spectrum, , ppm: 1.48 s (6H, CH3), 3.68 s (2H,
CH2), 7.26 s (2H, R2NH+2 ), 7.53 d (2H, HCCC, J
9.0), 8.20 d (2H, HCCN, J 9.0). Found, %: C 64.42;
H7.59; Cl18.95; N 6.80. C10H14ClN. Calculated,%:
5. Weigand, C. and Hilgetag, G., Organisch-Chemische
Experimentierkunst, Leipzig: Johann Ambrosis Barth.
6. Le, V.T., Cand. Sci. (Chem.) Dissertation, Ufa, 1999.
7. Organikum, organisch-chemisches Grundpraktikum,
Heidelberg: Johann Ambrosis Barth, 1996.
C 65.39; H 7.65; Cl 19.34; N 7.63. m/z: 183 M+ ,
+
+
134 (M CH2Cl) , 118 (M CH2Cl NH2) .
8. Poland Patent 101 164, 1979; Chem. Abstr., 1980,
vol. 92, P76102e.
1-Chloro-2-(p-ethoxyphenyl)-2-methylpropane
(III). To a mixture of 1 g (5 mmol) of phenol (XIII),
1.2 g of K2CO3 in 5 ml of dry acetone at 40 C while
stirring was added under argon 0.9 g (8 mmol) of
ethyl bromide. The stirring at 40 C was continued
for 15 h. Then the reaction mixture was cooled,
diluted with 20 ml of water, and the products were
extracted into ether. The extract was washed with
NaOH solution, with solution of NaCl, and dried
with calcium chloride. The solvent was evaporated,
the product was subjected to column chromatography
on silica gel, eluent hexane ether, 10: 1. We obtained
0.77 g (67%) of compound III.
9. Yanovskaya, L.A. and Yufit, S.S., Organicheskii sin-
tez v dvukh fazakh (Organic Synthesis in Two-Phases
Systems), Moscow: Khimiya, 1982, p. 58.
10. Japan Patent 58 88 336, 1983; Chem. Abstr., 1983,
vol. 99, 122010t.
11. Kucherenko, A.P., Belous, D.D., Martyushen-
ko, V.A., Promonenkov, V.K., Bliznyuk, A.N., and
Belyaeva, A.A., Abstracts of Papers, All-Union Conf.
Reakhimtekhnika-3 , Dnepropetrovsk, 1989;
12. Nagaki, K., Nakayama, M., and Hayasaki, Sh., Bull.
Chem. Soc. Jpn., 1978, vol. 51, no. 11, pp. 3273
3276 (Eng).
13. Coats, J.R., Williams, J.W., Chang, C., Lee, A.H.,
and Metcalf R.L., Environ. Toxicol. and Chem.,
1989, vol. 8, no. 1, pp. 45 52.
2-(4-Ethoxyphenyl)-2-methylpropyl phenoxy-
benzyl ether (I). A mixture of 0.5 g (2.4 mmol) of
2-(4-ethoxyphenyl)-2-methylpropyl chloride (III),
0.68 g (3.4 mmol) of 3-phenoxybenzyl alcohol, and
0.5 g of KOH powder in 2 ml of DMSO was heated
to 110 120 C under argon atmosphere for 15 h. The
reaction mixture was cooled, diluted with water,
extracted with ether, the extract was washed in
succession with solutions of NaOH and NaCl, and
dried on CaCl2. The solvent was evaporated, and
1.1 g of the mixture obtained was subjected to
column chromatography on silica gel, eluent hexane
14. Ionin, B.I., Ershov, B.A., and Kol,tsov, A.I.,
YaMR-spektroskopiya v organicheskoi khimii (NMR
Spectroscopy in Organic Chemistry), Leningrad:
Khimiya, 1983, pp. 153 154.
15. Strakov, L.Ya., Gudrinietse, E.Yu., Nevin,sh, A.F.,
and Vanag, G.Ya., Zh. Obshch. Khim., 1960, vol. 30,
no. 12, pp. 3967 3972.
16. Oae, Sh., Furukawa, N., Kise, M., and Kawani-
shi, M., Bull. Chem. Soc. Jpn., 1996, vol. 39, no. 6,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 11 2002