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1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-1-hexanone → 2-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 2186546
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2186546
[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=[CH:4][C:3]1=2>C(O)C.[Pd].Cl>[CH2:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:21])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 224568761-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-1-hexanone

Produkt 1

HCID 230025302-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthaleneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 13.8 g of 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-1-hexanone (from Example 1.1) in 200 ml ethanol abs., containing 2 g of palladium on carbon 10% and 3 drops of HCl 25%, was subjected to H2 atmosphere for 3 hours (until consumption of theoretical amount H2 is reached and thin layer chromatography showed no more starting material was present). The mixture was filtered and concentrated in vacuo. The residue was diluted in 200 ml ether, dried over MgSO4, filtered and concentrated in vacuo, giving a yellow oil. The crude product was distilled under vacuum (T=120° C. at 0.08 bar), yielding a pale yellow oil (12.1 g). B.p. 120° C. at 0.08 bar.

Aufarbeitung

  1. custom(until consumption of theoretical amount H2
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted in 200 ml ether
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customgiving a yellow oil
  9. distillationThe crude product was distilled under vacuum (T=120° C. at 0.08 bar)

Quellen und Nachweise

ORD-Eintrag
ord-d77808b5a6794a1c88c7062489e0f284
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06403810B2

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