NORCAMPHORICACID Chemical Properties

Melting point:

121.5 °C

Boiling point:

320.7±25.0 °C(Predicted)

Density 

1.396±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.23±0.40(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H10O4/c8-6(9)4-1-2-5(3-4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)

InChIKey

LNGJOYPCXLOTKL-UHFFFAOYSA-N

SMILES

C1(C(O)=O)CCC(C(O)=O)C1

NORCAMPHORICACID Usage And Synthesis

Uses

Cyclopentane-?1,?3-?dicarboxylic Acid is used in the study of ruthenium-?catalyzed oxidation of alkenes and monoenic fatty acids.

Synthesis

A mechanical stirrer, J-KEM temperature controller and nitrogen inlet were assembled in a 22 L three-necked round bottom flask. Norbornene (200 g, 2.123 mol), ethyl acetate (1.95 L) and acetonitrile (1.95 L) were added sequentially. The reaction mixture was cooled to 5 °C using an acetone/dry ice bath. Ruthenium trichloride (9.69 g, 46.72 mmol) was added in batches, followed by a slow dropwise addition of an aqueous (2.925 L) suspension of sodium periodate (1.816 kg, 8.707 mol) over 30 min. The reaction became exothermic and was controlled between 10 °C and 15 °C. After 90 min, the reaction mixture thickened significantly, stirring was difficult, and the temperature rose rapidly to 39 °C (exotherm was controlled by replenishing the cooling bath with large amounts of dry ice). The reaction mixture was cooled to 20 °C, the cooling bath was withdrawn and stirring was continued overnight at room temperature. The reaction mixture was filtered through a diatomaceous earth pad to remove solids and the filtrate was concentrated until solids precipitated. The solid was ground with hexane (2 L), filtered and washed with hexane (2 x 500 mL) to give 195 g of cyclopentane-1,3-dicarboxylic acid (58% yield). The product was characterized by 1H NMR (500 MHz, DMSO-d6): δ 12.07 (s, 2H), 2.66-2.73 (m, 2H), 2.06-2.12 (m, 1H), 1.85-1.89 (m, 1H), 1.72-1.85 (m, 4H).

References

[1] Tetrahedron Letters, 2005, vol. 46, # 18, p. 3201 - 3203
[2] Russian Journal of Applied Chemistry, 2011, vol. 84, # 2, p. 236 - 242
[3] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3123 - 3126
[4] Australian Journal of Chemistry, 1985, vol. 38, # 11, p. 1705 - 1718
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 10, p. 3480 - 3491

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