bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride Chemical Properties

Melting point:

148 °C

Boiling point:

340.9±42.0 °C(Predicted)

Density 

1.324

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

soluble in Acetone

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C10H10O3/c11-9-7-5-1-2-6(4-3-5)8(7)10(12)13-9/h1-2,5-8H,3-4H2

InChIKey

YIHKILSPWGDWPR-UHFFFAOYSA-N

SMILES

C1(=O)C2C(C3CCC2C=C3)C(=O)O1

Safety Information

HS Code 

2932990090

bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride Usage And Synthesis

Synthesis

1,3-Cyclohexadiene (36.40 g, 0.4543 mol) and maleic anhydride (29.10 g, 0.2968 mol) were added to a 250 mL Schlenk flask equipped with a magnetic stirrer. After installing the condenser tube, the system was placed under dynamic nitrogen protection and the reaction mixture was heated to 60°C. After 5 minutes of heating, maleic anhydride was completely dissolved to form a bright yellow solution, after which reflux was initiated. 1,3-Cyclohexadiene contributed to the solidification of the reaction mixture into light yellow crystals within 25 minutes of the onset of heating. After 3 hours of continued reaction, unreacted 1,3-cyclohexadiene was removed by distillation under reduced pressure. The resulting yellow crystalline solid was recrystallized from 200 mL of standard ethanol to give Diels-Alder adduct 5 as 46.54 g of white crystalline solid (88% yield). 1H NMR (700 MHz, CDCl3, 25 °C): δ = 1.43 (d, J = 7.7 Hz, 2H, CH2 cyclohexene), 1.62 (d, J = 7.7 Hz, 2H, CH2 cyclohexene), 3.15 (t, 2H, -CH-CO), 3.25 (m, 2H, methine cyclohexene), 6.33 (dd, J = 7.7 Hz, 4.2 Hz, 3.5 Hz, 2H, -CH=CH-). 13C NMR (700 MHz, CDCl3, 25°C): δ = 22.98 (CH2, cyclohexene), 31.63 (methine cyclohexene), 44.77 (-CH-CO), 133.05 (-C=C-), 172.83 (CO). IR (cm-1): 3055 (=C-H stretch), 2980-2870 (C-H stretch), 1867-1766 (C=O stretch), 1462-1322 (C-H bend), 1238-1177 (C-O stretch), 1075-684 (C-H out-of -plane bend). LC-MS: m/z 179.07 (M+), 151.07, 147, 133, 123, 105, 79, 73.

References

[1] Patent: US2013/324688, 2013, A1. Location in patent: Paragraph 0039; 0041; 0085-0087
[2] Heterocycles, 2006, vol. 68, # 11, p. 2259 - 2267
[3] Journal of the Chemical Society, 1929, p. 906
[4] Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 98
[5] Justus Liebigs Annalen der Chemie, 1930, vol. 478, p. 141

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