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Short Note

Esterification and hydrolysis under microwave irradiation

by
Krunal G. Desai
* and
Kishor R. Desai
Department of Chemistry, Synthetic Organic Chemistry Research Laboratory, Veer Narmad South Gujarat University, Surat-395 007 (Gujarat), India
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(3), M477; https://doi.org/10.3390/M477
Submission received: 27 June 2005 / Accepted: 6 September 2005 / Published: 31 March 2006
Versions Notes

Molbank 2006 m477 i001
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) δ (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) δ (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.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Veer Narmad South Gujarat University, Surat for providing research facilities and one of the author (Krunal Desai) is thankful to the Gujarat Council On Science & Technology, Gandhinagar for financial support (Grant No. GUJCOST/200389/MRP/2003-04/10689). Authors are also thankful to CDRI, Lucknow for providing spectral and analytical data of the compounds.

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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MDPI and ACS Style

Desai, K.G.; Desai, K.R. Esterification and hydrolysis under microwave irradiation. Molbank 2006, 2006, M477. https://doi.org/10.3390/M477

AMA Style

Desai KG, Desai KR. Esterification and hydrolysis under microwave irradiation. Molbank. 2006; 2006(3):M477. https://doi.org/10.3390/M477

Chicago/Turabian Style

Desai, Krunal G., and Kishor R. Desai. 2006. "Esterification and hydrolysis under microwave irradiation" Molbank 2006, no. 3: M477. https://doi.org/10.3390/M477

APA Style

Desai, K. G., & Desai, K. R. (2006). Esterification and hydrolysis under microwave irradiation. Molbank, 2006(3), M477. https://doi.org/10.3390/M477

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