COMPOUNDS OF THE MENTHANE SERIES.
811
1
solved, the mixture turned bright blue. It was heated
for 48 h at 90°C until the blue color disappeared com-
pletely, cooled, and treated with 0.5 L of water. The
organic phase was separated, the aqueous phase was
extracted with diethyl ether (3×100 mL), the extracts
were combined with the organic phase and dried over
Na2SO4, and the solvent was distilled off. Yield 70–
75%, conversion 75% (1), 66% (2), 80% (3). Frac-
tionation in a column with 60 theoretical plates gave
primary menthene alcohols.
cm–1: 3370, 1040 (OH), 1665 (C=C). H NMR spec-
trum, δ, ppm: 0.91 d (3H, C10H3, J = 6.8 Hz), 1.50–
2.15 m (9H, OH, CH2), 1.65 s (3H, C7H3), 2.96 m
(1H, CH), 3.44 m and 3.51 m (2H, CH2O). Found, %:
C 77.43; H 11.58. C10H18O. Calculated, %: C 77.87;
H 11.76.
(2-Isopropylcyclohex-2-en-1-yl)methanol (19).
Purity 92% (GLC), bp 85–87°C (5 mm), d240 = 0.9529,
nD20 = 1.4900; MRD 46.80, calcd. 47.24. IR spectrum, ν,
1
cm–1: 3370, 1040 (OH), 1665 (C=C). H NMR spec-
trum, δ, ppm: 0.91 d (3H, C10H3, J = 6.8 Hz), 1.50–
2.15 m (9H, OH, CH2), 1.65 s (3H, C7H3), 2.96 m
(1H, CH), 3.44 m and 3.51 m (2H, CH2O). Found, %:
C 78.34; H 11.38. C10H18O. Calculated, %: C 77.87;
H 11.76.
2-(2-Methylcyclohex-1-en-1-yl)propan-1-ol (11).
Purity 98% (GLC), bp 78–79°C (3 mm), d240 = 0.9463,
nD20 = 1.4910; MRD 47.21, calcd. 47.24. IR spectrum,
ν, cm–1: 3370, 1040 (OH), 1665 (C=C). 1H NMR spec-
trum, δ, ppm: 0.91 d (3H, C10H3, J = 6.8 Hz), 1.50–
2.15 m (9H, OH, CH2), 1.65 s (3H, C7H3), 2.96 m
(1H, CH), 3.44 m and 3.51 m (2H, CH2O). Found, %:
C 78.08; H 11.55. C10H18O. Calculated, %: C 77.87;
H 11.76.
The authors thank junior researcher T.N. Overchuk
(I.N. Ul’yanov Chuvash State University) for her
participation in the experimental work.
2-(6-Methylcyclohex-1-en-1-yl)propan-1-ol (12).
Purity 98% (GLC), bp 73–74°C (5 mm), d240 = 0.9448,
nD20 = 1.4880; MRD 47.03, calcd. 47.24. IR spectrum, ν,
cm–1: 3370, 1035 (OH), 3060, 1675, 815 (C=CH).
1H NMR spectrum, δ, ppm: 0.99 d (3H, C7H3, J =
7.0 Hz), 1.03 d (3H, C10H3, J = 6.8 Hz), 1.45–2.45 m
(7H, OH, CH2), 2.90 m (1H, CH), 3.45 m and 3.53 m
(2H, CH2O), 5.51 m (1H, C=CH). Found, %: C 77.59;
H 11.90. C10H18O. Calculated, %: C 77.87; H 11.76.
REFERENCES
1. Carmona, P., Bellanato, J., and Hidalgo, A., Rev.
Agroquim. Tecnol. Aliment., 1974, vol. 14, p. 375.
2. Streibl, M., Ubik, K., Herout, V., Konečný, K., and
Kolátorová, E., Collect. Czech. Chem. Commun., 1975,
vol. 40, p. 1028.
3. Nomura, M., Fujihara, Y., and Matsubara, Y., Nippon
Kagaku Kaishi, 1978, vol. 8, p. 1162.
4. Chastain, D.E., Mody, N., and Majetich, G., US Patent
no. 5 994 598A, 1998; Ref. Zh., Khim., 2001,
no. 22-190, P132.
2-(4-Methylcyclohex-3-en-1-yl)propan-1-ol (16).
Purity 95% (GLC), bp 99–100°C (1 mm), d420
=
0.9442, nD20 = 1.4845; MRD 46.90, calcd. 47.24. IR
spectrum, ν, cm–1: 3055, 1035 (OH), 3060, 1675, 815
(C=CH). 1H NMR spectrum, δ, ppm: 0.79–2.64 m (8H,
CH2, CH), 0.86 d (3H, CHCH3, J = 6.75 Hz), 1.65 s
(3H, CH3C=), 2.79 s (1H, CH), 3.38 m (2H, CH2O),
5.30 m (1H, C=CH). Found, %: C 78.01; H 11.92.
C10H18O. Calculated, %: C 77.87; H 11.76.
5. Mac-Kenzie, B.D., Angelo, M.M., and Wolinsky, J.,
J. Org. Chem., 1979, vol. 44, p. 4042.
6. Williams, D.R. and Phillips, J.G., J. Org. Chem., 1981,
vol. 46, p. 5452.
7. Veno, K., Suemune, H., Saeki, S., and Sakai, K., Chem.
Pharm. Bull., 1985, vol. 33, p. 4021.
8. Suemune, H., Kawahara, T., and Sakai, K., Chem.
Pharm. Bull., 1986, vol. 34, p. 550.
2-(4-Methylcyclohex-1-en-1-yl)propan-1-ol (17).
Purity 95% (GLC), bp 68–70°C (7 mm), d240 = 0.9346,
nD20 = 1.4820; MRD 47.04, calcd. 47.24; published data
[22]: bp 105–109°C (10 mm). IR spectrum, ν, cm–1:
3390, 1040 (OH), 3060, 1665, 820 (C=CH), 1375
9. Bazyl’chik, V.V., Fedorov, P.I., and Odinokov, V.N.,
Zh. Org. Khim., 1990, vol. 26, p. 1929.
10. Bazyl’chik, V.V., Overchuk, T.N., and Fedorov, P.I.,
USSR Inventor’s Certificate no. 1 685 912, 1990; Byull.
Izobret., 1991, no. 39.
1
(CH3). H NMR spectrum, δ, ppm: 0.81–0.98 m (6H,
CH3), 1.09–2.21 m (8H, CH, CH2), 2.68 m (1H, OH),
3.29 m (2H, CH2O), 5.33 m (1H, C=CH). Found, %:
C 77.58; H 11.45. C10H18O. Calculated, %: C 77.87;
H 11.76.
11. Organikum. Organisch-chemisches Grundpraktikum,
Berlin: Wissenschaften, 1976, 15th edn. Translated
under the title Organikum. Praktikum po organicheskoi
khimii, Moscow: Mir, 1979, vol. 2, p. 194.
12. Pinder, A.R. and Smith, H., J. Chem. Soc., 1954, p. 113.
(2-Isopropylcyclohex-1-en-1-yl)methanol (18).
Purity 96% (GLC), bp 90–91°C (5 mm), d240 = 0.9517,
nD20 = 1.4930; MRD 47.10, calcd. 47.24. IR spectrum, ν,
13. Grinenko, G.S. and Maksimov, V.I., Dokl. Akad. Nauk
SSSR, 1959, vol. 29, p. 2056.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 6 2016