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Germacrene D → beta-Bourbonene

HRID 372146
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 5317570Germacrene D

Product 1

HCID 62566beta-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

  • customthe solution thus obtained
  • 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
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04089764

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes