Acetophenone → β-bourbonene

HRID 372147Notes

Reaction equation

HRID 372147 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].C(C1C=CC=CC=1)(=O)C>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

4

Reactant 2

HCID 7410AcetophenoneHCID 5317570(-)-Germacrene D

Product 1

HCID 62566β-bourboneneYield 92.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

60 kg of leaves of Solidago gigantea Aiton var. leiophylla Fern. was steam-distilled and 120 g of essential oil was obtained. 100 g of the essential oil containing 40 g of germacrene D was dissolved in 20 l of n-hexane with addition of 50 g of acetophenone and was subjected to internal irradiation with the light of high pressure mercury lamp for 12 hours. After fractional distillation under reduced pressure, 37 g of β-bourbonene was obtained. (Conversion Ratio: 93%)

Workup

  1. customwas subjected to internal irradiation with the light of high pressure mercury lamp for 12 hours
  2. distillationAfter fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-95a799c704ec4e86acc3f7e948a816a6
Source dataset
uspto-grants-1978_05
Patent number
US04089764

Reaction notes

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