Camphor → Borneol

HRID 1168044Notes

Reaction equation

HRID 1168044 reaction equation
[2H-].[Al+3].[Li+].[2H-].[2H-].[2H-].[C:7]12([CH3:17])[C:14]([CH3:16])([CH3:15])[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:8]2=[O:9].[H-]>CCOCC>[CH3:15][C:14]1([CH3:16])[C:7]2([CH3:17])[CH:8]([OH:9])[CH2:10][CH:11]1[CH2:12][CH2:13]2

Participants

5

Reactant 3

HCID 2537CamphorHCID 166653HydrideHCID 86600389Aluminum;lithium;deuteride

Product 1

HCID 64685BorneolYield 98.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of lithium aluminum deuteride (LiAlD4) (0.012 g) in anhydrous ether (1 mL) was added, with stirring, camphor (0.1 g) in ether (2 mL), followed by heating at reflux for 3 hours. After cooling to room temperature, the excess hydride was decomposed by addition of moist ether, then the organic layer was washed with brine, dried (Na2CO4) and evaporated to give a quantitative yield of deuteriated isoborneol (0.1 g). 2H NMR (hexanes): δ 3.75. See B. Belleau, J. Am. Chem. Soc., 82, p. 5751 (1960).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 3 hours
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2CO4)
  5. customevaporated

Sources & evidence

ORD record
ord-bf1a3af668ac4abbb310bc752e1b641b
Source dataset
uspto-grants-2003_09
Patent number
US06620972B2

Reaction notes

Loading…