Hydrogen Peroxide → 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene

HRID 1019353Notes

Reaction equation

HRID 1019353 reaction equation
[OH:1][OH:2].[OH-].[Na+].[CH3:5][C:6]1[CH2:11][CH2:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1>CO>[CH3:13][CH:12]([C:9]12[O:2][O:1][C:6]([CH3:5])([CH:11]=[CH:10]1)[CH2:7][CH2:8]2)[CH3:14]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 7462alpha-TerpineneHCID 14798Sodium Hydroxide

Product 1

HCID 105451-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-eneYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 30° C., 230 μl of H2O2 (50%) and 200 μl of 5M NaOH were successively added to a solution of 325 μl of α-terpinene and 143.6 mg of La(NO3)3.xH2O in 4 ml of methanol, whereupon a white precipitate formed. After 3.5 hours and after 21 hours, two further 230 μl portions of H2O2 (50%) were added to the mixture. After 24.5 hours, the reaction mixture was centrifuged, and the solution was decanted from the catalyst. The solvent was evaporated and the residue was dissolved in CDCl3 and analyzed using NMR. The reaction mixture was also analyzed by means of HPLC (MeOH/H2O 90/10; 260 nm). The analyses gave a conversion of 10% and a yield of >90% of ascaridol.

Workup

  1. waitafter 21 hours
  2. waitAfter 24.5 hours
  3. customthe solution was decanted from the catalyst
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in CDCl3
  6. customThe analyses gave a conversion of 10%

Sources & evidence

ORD record
ord-4738c71cd58a40a588ca5b9523aabde9
Source dataset
uspto-grants-2002_11
Patent number
US06486360B1

Reaction notes

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