Molbank 2006, M477 |
Esterification and hydrolysis under microwave irradiation
Krunal G. Desai* and Kishor R. Desai
Department of Chemistry, Synthetic Organic Chemistry Research
Laboratory,
Tel: (0261) 2258384, Fax: (0261) 2258384 e-mail: [email protected]
*Author to whom correspondence should be
addressed
Received: 27 June 2005 / Accepted: 6 September 2005 / Published: 31 March 2006
Keywords: esterification, ammonolysis, microwave
effect.
p-methoxy benzoicacid 1 (1.67 g, 0.01 mole) and catalytic amount of conc. H2SO4
(2-3 drops) in absolute methanol (30 mL) was taken in
RBF placed in a microwave oven and irradiated (400w, 61-62oC) for
2.5 min [1]. Upon completion of reaction (monitored by TLC), using petroleumether-ethylacetate (8:2) as the eluent solvent system. The reaction mixtures was allowed to
attain room temperature and treated with cold water. The solid separated was
filtered, washed with water and recrystallised from
ethanol to furnish compound 2, yield
90%.
Methyl ester of p-methoxy benzoicacid 2 (1.66 g, 0.01 mole) and hydrazine hydrate (0.9 mL, 0.01 mole) in ethanol (20 mL) was taken in RBF placed in a microwave oven and irradiated (450w, 76-78oC) for 3.5 min [1]. After completion of reaction (monitored by TLC), using petroleumether-ethylacetate (8:2) as the eluent solvent system. The mixture was cooled and the resulting solid was filtered, dried and recrystallized from ethanol to get compound 3, yield 83%.
Melting point: 88 oC 2 and 136 oC 3.
IR (KBr) (cm-1):
2 1722 (>C=O of ester), 1225,
1044 (C-O-C), 3023 (C-H, aromatic ring), 1510 (C=C, aromatic ring), 2825 (-OCH3).
3 1661 (>C=O of amide),
3355, 3382 (-NHNH2), 2837 (-OCH3), 3028, 1522 (C-H, C=C,
aromatic ring).
1H-NMR (CDCl3-DMSO-d6) (400 MHz) ¦Ä (ppm): 2 6.70-7.90 (4H, m, Ar-H), 4.0 (3H, s, -COOCH3), 3.87 (3H, s, -OCH3). 3 6.85-7.96 (4H, m, Ar-H), 4.41 (2H, s, -NH2), 7.85 (1H, s, -CONH-), 3.89 (3H, s, -OCH3).
13C-NMR (CDCl3-DMSO-d6) (62.90 MHz) ¦Ä (ppm): 2 56.60 (-OCH3), 115.29-134.1 (aromatic carbons), 170 (>C=O of ester), 20 (-COOCH3). 3 57.68 (-OCH3), 117.31-130.0 (aromatic carbons), 162 (>C=O of amide).
MS (m/z): 2 166 (M+) (C9H10O3+), 135 (C8H7O2+), 107 (C7H7O+), 59 (C2H3O2+), 31 (CH3O+). 3 166 (M+) (C8H10O2N2+), 135 (C8H7O2+), 107 (C7H7O+), 31 (N2H3+), 16 (NH2+).
Elemental Analysis: Calculated for 2 C9H10O3: C 65.06, H 6.02. Found: C 65.10, H 6.00.
Elemental Analysis: Calculated for 3 C8H10N2O2: C 72.18, H 6.02, N 16.86. Found: C 72.20, H 6.04, N, 16.89.
The authors thank the
References
1. Desai, K. G.; Desai, K. R. Indian J. Chem. (Sec-B). 2005, (In Press).
Sample Availability: Available from MDPI.
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