3-Hydroxycyclopentadecene → 2-Cyclopentadecenone

HRID 2398710Notes

Reaction equation

HRID 2398710 reaction equation
[OH:1][CH:2]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1>CCCCCCC.[O-2].[O-2].[Mn+4]>[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:2](=[O:1])[CH:3]=1

Participants

4

Reactant 1

HCID 544205383-Hydroxycyclopentadecene

Product 1

HCID 540403452-Cyclopentadecenone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8900HeptaneSolvent

Procedure

3-Hydroxycyclopentadecene (20.1 g) in dried n-heptane was stirred at room temperature and a total of 100 g manganese dioxide was added in four batches of 50, 25, 15 and 10 g respectively over a period of 6 hours. After 22 hours the conversion as indicated by GLC was 100%. The mixture was filtered and the filtrate was then stirred with active charcoal and refiltered. The solvent was then removed from the filtrate under reduced pressure to yield the required product.

Workup

  1. filtrationThe mixture was filtered
  2. customThe solvent was then removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-7aa3841707cb44ddaca7952cabb47e92
Source dataset
uspto-grants-1977_05
Patent number
US04025562

Reaction notes

Loading…