Borneol → Camphor

HRID 1873113Notes

Reaction equation

HRID 1873113 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6]2([CH3:10])[CH:7]([OH:9])[CH2:8][CH:3]1[CH2:4][CH2:5]2.[O-]Cl.[Na+]>C(O)(=O)C>[C:6]12([CH3:10])[C:2]([CH3:11])([CH3:1])[CH:3]([CH2:4][CH2:5]1)[CH2:8][C:7]2=[O:9]

Participants

4

Reactant 2

HCID 64685BorneolHCID 23665760Sodium Hypochlorite

Product 1

HCID 2537CamphorYield 96.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a vigorously stirred solution of 600 g (3.89 mol) of (-)-borneol in 1.5 L of glacial acetic acid at 0° C. was added 7.5 L of household bleach (Chlorox™) over a period of 1 h. After 30 min the solid (800 g) was collected by filtration and dissolved in 2 L of hexane. The solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated to give 570 g (96%) of camphor.

Workup

  1. filtrationAfter 30 min the solid (800 g) was collected by filtration
  2. dissolutiondissolved in 2 L of hexane
  3. washThe solution was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14e56dfedfa347b8a731ca6203ed8127
Source dataset
uspto-grants-2000_08
Patent number
US06111144

Reaction notes

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