Hydrogen Peroxide → (+)-Sclareol oxide

HRID 399619Notes

Reaction equation

HRID 399619 reaction equation
[CH3:1][C@@:2]12[C@@H:11]([CH2:12][CH2:13][C@@:14]([OH:18])([CH:16]=C)C)[C@@:10](O)([CH3:19])[CH2:9][CH2:8][C@H:7]1[C:6]([CH3:22])([CH3:21])[CH2:5][CH2:4][CH2:3]2.O=[O+][O-].[OH-].[K+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[CH3:16][C:14]1[O:18][C@@:2]2([CH3:1])[C@@H:11]([C@:10]3([CH3:19])[C@@H:5]([CH2:4][CH2:3]2)[C:6]([CH3:21])([CH3:22])[CH2:7][CH2:8][CH2:9]3)[CH2:12][CH:13]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 24823OzoneHCID 163263Sclareol

Product 1

HCID 7057250(+)-Sclareol oxideYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

40.6 g of sclareol (0.132 mol) in 300 ml methanol was ozonolysed at 20°-25° C. using a Gebr. Herrmann LAB-50-1 lab ozoniser operating at 130V, with flow rate at 61/hr, under which conditions 0.05 mol/hr of ozone was generated. The reaction was complete in 3 hrs whereafter the reaction mixture was poured into a mixture of 19 g KOH and 38 ml H2O2 in 500 ml of water and stirred for 30 min. The suspension was extracted three times with 100 ml toluene. the organic layer was washed with 100 ml 0.1 mol sodium thiosulphate solution and dried over Mg sulphate. Thereafter toluene was removed at 55° C. under reduced pressure. 33.6 g (97.4% yield) of pure sclareol oxide was obtained.

Workup

  1. customwas ozonolysed at 20°-25° C.
  2. extractionThe suspension was extracted three times with 100 ml toluene
  3. dry with materialdried over Mg sulphate
  4. customThereafter toluene was removed at 55° C. under reduced pressure

Sources & evidence

ORD record
ord-a7b5d6b53ede488183ffa2824f1978c5
Source dataset
uspto-grants-1998_10
Patent number
US05821375

Reaction notes

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