(-)-Germacrene D → β-bourbonene

HRID 372146Notes

Reaction equation

HRID 372146 reaction equation
[CH3:1][C:2]1=[CH:3][CH2:4][CH2:5][C:6]([CH:8]=[CH:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:12]1)=[CH2:7]>CCCCCC>[CH3:14][CH:13]([C@H:10]1[C@@H:11]2[C@H:12]3[C:2](=[CH2:1])[CH2:3][CH2:4][C@H:5]3[C@:6]2([CH3:7])[CH2:8][CH2:9]1)[CH3:15]

Participants

3

Reactant 1

HCID 5317570(-)-Germacrene D

Product 1

HCID 62566β-bourboneneYield 92.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

100 g of the essential oil of Solidago altissima L. was distilled under reduced pressure and 14 g of germacrene D was obtained. 14 g of the germacrene D was dissolved in 2.6 l of n-hexane and the solution thus obtained was subjected to internal irradiation with the light of low pressure mercury lamp for 190 hours. 13 g of β-bourbonene was obtained. In the case of the irradiation with the light of high pressure mercury lamp the similar result was obtained. (Note: The above-mentioned irradiation time is for 14 g of germacrene D. If irradiation is to be given to 100 g of essential oil containing 40 g of germacrene D, irradiation time required will be about 540 hours.)

Workup

  1. customthe solution thus obtained
  2. customwas subjected to internal irradiation with the light of low pressure mercury lamp for 190 hours

Sources & evidence

ORD record
ord-152bb999da64482ba7beff907286efe2
Source dataset
uspto-grants-1978_05
Patent number
US04089764

Reaction notes

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