METHYLATION OF ALIPHATIC AND AROMATIC CARBOXYLIC ACIDS
19
the residue was distilled at atmospheric or reduced
pressure, or crystallized.
Н 8.81. С6Н10О2. Calculated, %: С 63.14; Н 8.83. М
114.1424.
Methyl p-methylbenzoate (2a). Yield 99%, mp 32–
33°С (methanol) (mp 33°C [9]). 13С NMR spectrum,
δС, ppm: 21.53 (СН3), 50.92 (ОСН3), 127.15 (С1),
128.71 (С3,5), 128.90 (С2,6), 142.65 (С4), 165.92
(С=О). Found, %: С 71.87; Н 6.68. С9Н10О2. Cal-
culated, %: С 71.98; Н 6.71. М 150.1745.
Dimethyl (1R,3S)-1,2,2,3-tetramethylcyclopentane-
1,3-dicarboxylate (22a). Yield 98%, bp 112–112.5°С
(3 mmHg). 13С NMR spectrum, δС, ppm: 9.82
(СН3С1), 10.70 (СН3С3), 17.40 and 19.22 (СН3С2),
33.93 (С5), 33.94 (С4), 52.00 (ОСН3), 52.04 (ОСН3),
53.03 (С2), 55.38 (С1), 56.20 (С3), 177.05 (С=О),
177.07 (С=О). Found, %: С 64.39; Н 9.13. С13Н22О4.
Calculated, %: С 64.44; Н 9.15. М 242.3113.
Methyl p-methoxybenzoate (3a). Yield 98%, mp
48–49°С (methanol) (mp 46°С [9]). 13С NMR spec-
trum, δС, ppm: 51.62 (ОСН3), 55.56 (ОСН3), 113.77
(С3,5), 122.53 (С1), 131.44 (С2,6), 163.34 (С4), 166.32
(С=О). Found, %: С 64.98; Н 6.02. С9Н10О3. Cal-
culated, %: С 65.05; Н 6.07. М 166.1739.
Dimethyl isophthalate (24a). Yield 98%, mp 68–
69°С {bp 124°C (2 mmHg) [9]}. 13С NMR spectrum,
δС, ppm: 53.16 (2ОСН3), 128.37 (С5), 130.45 (С2),
130.75 (С1,3), 133.56 (С4,6), 165.23 (2 С=О). Found,
%: С 61.76; Н 5.15. С10Н10О2. Calculated, %: С 61.85;
Н 5.19. М 194.184.
Methyl p-bromobenzoate (4a). Yield 90%, mp 31–
32°C (methanol) (mp 32°С [9]). 13С NMR spectrum,
δС, ppm: 52.16 (ОСН3), 127.89 (С4), 128.96 (С1),
131.43 (С2,6), 132.02 (С3,5), 165.80 (С=О). Found, %:
С 44.58; Н 3.22, Br 37.11. С8Н7BrО2. Calculated, %:
С 44.68; Н 3.28; Br 37.17. М 215.0439.
ACKNOWLEDGMENTS
This work was performed using the equipment of
the Center for Collective Usage “Agidel.”
REFERENCES
Methyl p-chlorobenzoate (5a). Yield 95%, mp 44–
45°С (methanol) (mp 44°С [9]). 13С NMR spectrum,
δС, ppm: 52.16 (ОСН3), 127.52 (С3,5), 128.36 (С1),
131.44 (С2,6), 138.82 (С4), 166.27 (С=О). Found, %: С
56.28; Н 4.12, Cl 20.73. С8Н7ClО2. Calculated, %: С
56.32; Н 4.14; Cl 20.78. М 170.5929.
1. Khimicheskaya entsiklopediya (Chemical Encyclopedia),
Knunyants, I.L. and Zefirov, N.S., Eds., Moscow:
Sovetskaya Entsiklopediya, 1998, vol. 5, p. 508.
2. Mitusova, T.N., Polina, E.V., and Kalinina, M.V.,
Sovremennyye dizel’nyye topliva i prisadki k nim
(Modern Diesel Fuels and Additives to Them),
Moscow: Tekhnika, 2002, p. 64.
3. Reutov, O.A., Kurts, A.L., and Butin, K.P., Orga-
nicheskaya khimiya (Organic Chemistry), Moscow:
Mosk. Gos. Univ., 1999, ch. 3, p. 1451.
4. Cram, D.J. and Hammond, G.S., Organic Chemistry,
New York: McGraw-Hill, 1964, p. 715.
5. Selva, M. and Tundo, P., J. Org. Chem., 2006, vol. 71,
no. 4, p. 1464. doi 10.1021/jo0520792
6. Arico, F. and Tundo, P., Russ. Chem. Rev., 2010, vol. 79,
no. 6, p. 479. doi 10.1070/RC2010v079n06ABEH004113
7. Shieh, W.-C., Dell, S., and Repic, O., J. Org. Chem.,
2002, vol. 67, no. 7, p. 2191. doi 1021/jo011036s
8. Khusnutdinov, R.I., Shchadneva, N.A., Mayakova, Yu.Yu.,
Konovalova, Yu.S., Khazipova, A.N., Kutepov, B.I.,
Russ. J. Org. Chem., 2017, vol. 53, no. 2, p. 163. doi
10.1134/S107042801702004X
9. The Systematic Identification of Organic Compouds,
Shriner, R., Hermann, C., Morrill, T., Curtin, D., and
Fuson, R., Eds., Hoboken: J. Wiley and Sons, 2004,
p. 731.
Methyl m-methoxybenzoate (7a). Yield 98%, bp
109–109.5°С (6 mmHg) (bp 224°С [9]). 13С NMR
spectrum, δС, ppm: 52.42 (ОСН3), 56.16 (ОСН3),
113.95 (С2), 119.16 (С4), 121.86 (С6), 130.61 (С6),
129.25 (С5), 131.74 (С1), 159.42 (С3), 166.33 (С=О).
Found, %: С 64.99; Н 6.04. С9Н10О3. Calculated, %: С
65.05; Н 6.07. М 166.1739.
Methyl 2,4-dimethoxybenzoate (9a). Yield 99%,
mp 48–49°С (methanol) (mp 48–50°С [9]). 13С NMR
spectrum, δС, ppm: 51.48 (ОСН3), 55.67 (ОСН3),
55.88 (ОСН3), 98.84 (С3), 104.56 (С5), 112.84 (С1),
133.89 (С6), 162.15 (С2), 163.95 (С4), 165.99 (С=О).
Found, %: С 61.19; Н 6.11. С10Н12О4. Calculated, %:
С 61.22; Н 6.16. М 196.1998.
Methyl cyclobutanoate (20a). Yield 98%, bp 76.7–
13
77°С (60 mmHg). С NMR spectrum, δС, ppm: 18.89
(С3), 25.32 (С2,4), 37.90 (С1), 51.67 (ОСН3), 175.74
(С=О). Mass-spectrum, m/z, (Irel, %): 114 (20) [M]+,
84 (5), 83 (22), 72 (20), 55 (100). Found, %: С 63.09;
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 1 2018