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Methyl 6-formyl-8-methoxy-2-oxo-2H-chromene-4-carboxylate

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21413, P.O. Box 9028, Saudi Arabia.
Molbank 2004, 2004(1), M362; https://doi.org/10.3390/M362
Submission received: 13 September 2003 / Accepted: 4 February 2004 / Published: 24 February 2004
Molbank 2004 m362 i001
A mixture of Vanillin 1 (0.5 g, 3.3 mmol) and triphenylphosphine (0.86 g, 3.3 mmol) was dissolved in CH2Cl2. The reaction mixture was cooled in ice bath to -5 °C. Dimethylacetylenedicarboxylate (0.56 g, 3.3 mmol) in CH2Cl2 was added dropwise over a period of 10 min with stirring. The reaction mixture was then refluxed for 4-5 hours the solvent was removed under reduced pressure and the solid mass was purified by recrystalization from ethanol.
M.p. 182 °C (EtOH, uncorrected).
UV lmax (nm; EtOH)/e (dm3.mol-1.cm-1) 326/14000
IR nmax (cm-1; KBr Disk) 2956, 2865 (C-H, aldehydic), 1764 (C=O), 1725 (C=O), 1607 (C=C).
1H-NMR (400 MHz; CDCl3; Me4Si) dH 10.15 (s, 1H, CHO), 8.6 (s, 1H, H-3), 7.7 (s, 1H, H-5), 7. 4 (s, 1H, H-7), 4.2 (s, 6H, 2xCH3O).
13C-NMR dC 53, 56 , 110.6, 111.8, 116.5, 120.7, 123.6, 132.1, 132.7, 141.6, 148.4, 158.5, 190.5.
Anal.Calc. for C13H10O6 ( 262.215): C 59.55, H 3.84; found : C 59.23, H 3.95.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Issa, Y.; Rahim, H.-S.; Afsaneh, Z. Tetrahedron Letters 1998, 39(16), 2391.
  2. Johnson, J. R. Org. Reaction 1942, Vol. 1, 210.

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MDPI and ACS Style

Asiri, A.M. Methyl 6-formyl-8-methoxy-2-oxo-2H-chromene-4-carboxylate. Molbank 2004, 2004, M362. https://doi.org/10.3390/M362

AMA Style

Asiri AM. Methyl 6-formyl-8-methoxy-2-oxo-2H-chromene-4-carboxylate. Molbank. 2004; 2004(1):M362. https://doi.org/10.3390/M362

Chicago/Turabian Style

Asiri, Abdullah Mohamed. 2004. "Methyl 6-formyl-8-methoxy-2-oxo-2H-chromene-4-carboxylate" Molbank 2004, no. 1: M362. https://doi.org/10.3390/M362

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