Bicyclo[2.2.2]octane-1,4-dimethanol Chemical Properties

Melting point:

107-108 °C

Boiling point:

298.8±8.0 °C(Predicted)

Density 

1.137±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.94±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C10H18O2/c11-7-9-1-2-10(8-12,5-3-9)6-4-9/h11-12H,1-8H2

InChIKey

DLBHMXBDKPROEG-UHFFFAOYSA-N

SMILES

C12(CO)CCC(CO)(CC1)CC2

Safety Information

HS Code 

2906190090

Bicyclo[2.2.2]octane-1,4-dimethanol Usage And Synthesis

Synthesis

An ether solution of diethyl dicyclo[2,2,2]octane-1,4-cyclohexanedicarboxylate (3.0313 g, 11.91 mmol) was slowly added to an ether suspension of lithium aluminum hydride (856.9 mg, 23.84 mmol) under argon protection. The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the reaction was quenched by slow addition of 2 M sodium hydroxide solution and water. The reaction mixture was filtered and the solid salt was washed with ether. All ether layers were combined and dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure to give bicyclo[2.2.2]octane-1,4-dimethanol (1.7899 g, 88% yield). The product was characterized by 1H-NMR (600 MHz, CDCl3): δ 1.43 (s, 14H), 3.27 (s, 4H).

References

[1] Journal of Organic Chemistry, 1984, vol. 49, # 4, p. 665 - 670
[2] Journal of the American Chemical Society, 2008, vol. 130, # 24, p. 7659 - 7669
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1756 - 1760
[4] Journal of pharmaceutical sciences, 1971, vol. 60, # 10, p. 1534 - 1537
[5] Journal of the American Chemical Society, 2011, vol. 133, # 10, p. 3570 - 3581

Bicyclo[2.2.2]octane-1,4-dimethanol(826-45-9)Related Product Information

• Hexane
• 2,3,3a,5,6,6a-Hexahydropentalene-1,4-dione
• 2,3-NORBORNANEDICARBOXYLIC ACID
• BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID
• bicyclo[1.1.1]pentan-1-ylmethanol
• Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester
• ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)
• 5-Norbornene-2-carboxamide
• bicyclo[3.2.1]octane-2,4-dione
• Bicyclo[3.1.0]hexan-3-ol
• Bicyclo[1.1.1]pentane-1-carboxylic acid, methyl ester (9CI)
• 4-Aminobenzocyclobutene
• 4-Hydroxymethylbenzocyclobutene
• 4-Carboxylbenzocyclobutene
• bicyclo[1.1.1]pentane-1,3-dicarbonitrile
• Bicyclo[1.1.1]pentane-1-sulfonamide
• Bicyclo[1.1.1]pentane-1,3-dicarboxamide
• Bicyclo[1.1.1]pentane-1-carboxamide