Sodium Acetate → Bicyclo[3.2.1]octan-8-ol, 1,5-dimethyl-, 8-acetate

HRID 1732861Notes

Reaction equation

HRID 1732861 reaction equation
[CH3:1][C:2]12[CH:9](Br)[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[C:12]([O-:15])(=[O:14])[CH3:13].[Na+]>C(O)(=O)C.[Cu]Cl>[CH3:1][C:2]12[CH:9]([O:15][C:12](=[O:14])[CH3:13])[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 5323829HCID 5323829, compound

Product 1

HCID 173489Bicyclo[3.2.1]octan-8-ol, 1,5-dimethyl-, 8-acetate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent

Procedure

5 g of 1,5-dimethyl-8-bromobicyclo[3,2,1]octane was boiled under reflux for 18 hours in acetic acid in the presence of sodium acetate and copper(I) chloride. The reaction mixture was cooled and filtered, diluted with water and extracted with pentane. The pentane solution was washed with water and an aqueous sodium bicarbonate solution, dired, evaporated and fractionally distilled. 1,5-dimethyl-8-acetoxy-bicyclo[3,2,1]octane was obtained in good yield. 1,5-dimethyl-8-acetoxybicyclo[3,2,1]octane was also obtained in a similar manner starting from the 8-iodo compound described in Example 3.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additiondiluted with water
  4. extractionextracted with pentane
  5. washThe pentane solution was washed with water
  6. customevaporated
  7. distillationfractionally distilled

Sources & evidence

ORD record
ord-0eceffbef72246bdb33234096b68b253
Source dataset
uspto-grants-1980_12
Patent number
US04239707

Reaction notes

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