| Identification | Back Directory | [Name]
Bicyclo[2.2.2]octane-1,4-dimethanol | [CAS]
826-45-9 | [Synonyms]
Bicyclo[2.2.2]octane-1,4-diMethano
Bicyclo[2.2.2]octane-1,4-dimethanol
Bicyclo[2.2.2]octane-1,4-diyldiMethanol
1,4-Bis(hydroxymethyl)bicyclo[2.2.2]octane
[4-(hydroxymethyl)-1-bicyclo[2.2.2]octanyl]methanol | [Molecular Formula]
C10H18O2 | [MDL Number]
MFCD23135544 | [MOL File]
826-45-9.mol | [Molecular Weight]
170.25 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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