E-(4-Methylbenzylidene)succinic anhydride

Abdullah Mohamed Asiri

Chemistry Department, Faculty of Science, King abdul-Aziz University, Jeddah 21589, P. B. Box 80203, Saudia Arabia. Tel. (+696)-2-6952293, Fax (+696)-2-6952292, E-mail: [email protected]

Received: 26 September 2000 / Accepted: 16 November 2000 / Published: 25 December 2000

The title compound was obtained by dehydration of the corresponding diacid 1 (12.1 g, 55 mmol) by boiling in acetyl chloride (50 ml) for four hours. The excess acetyl chloride was removed under vacuum and the residue crystallised from ethanol to give the anhydride 2 as yellow crystals (5.1 g, 46%).

M.p. 210-212°C (EtOH, Uncorrected).

UV (EtOH) (e dm³.mol^-1.cm^-1): 291 (25000), 396 (5000).

IR (KBr, cm^-1): 1805 (C=O), 1751 (C=O).

¹H-NMR (400 MHz, CDCl₃): 7.85 (1H, s, HC=), 7.28 (2H, d, J 7.8 Hz), 7.19 (2H, d, J 7.8 Hz), 3.51 (2H, s, CH₂), 2.37 (3H, s, CH₃).

¹³C-NMR (100 MHz, CDCl₃): 21.3 (CH₃), 33.71 (CH₂), 129.2, 129.3, 132.3, 135.0, 141.5 (CH=C), 169.8 (C=O), 173.4 (C=O).

Anal. Calc. For C₁₂H₁₀O₃ (202.12): C, 71.30, H, 4.95; found : C, 71.11, H, 5.12.

References

1.	Stobbe, H. Ber. 1904, 37, 2236.
2.	Johnson, W. S.; Duab, G. H. Org. React. 1951, 6, 1.

Sample availability: available from the authors and MDPI.

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