(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene → (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene

HRID 35750

Reaktionsgleichung

Reaktionsgleichung von HRID 35750
Cl[CH2:2][C@@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:15])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH2:4]1.O.O.O.C([O-])(=O)C.[Na+]>[C].[Pd].C(O)(C)C>[CH3:16][C:5]1([CH3:17])[C:6]2[C:11](=[CH:10][C:9]([CH3:15])=[CH:8][CH:7]=2)[C:12]([CH3:14])([CH3:13])[C@@H:3]([CH3:2])[CH2:4]1

Komponenten

5

Edukt 2

HCID 13175029(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 23665404Sodium Acetate Trihydrate

Produkt 1

HCID 13175223(S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthaleneAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Into an autoclave, (S)-3-(chloromethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene 200 mg; 0.798 mmol), isopropanol (10 ml), sodium acetate trihydrate (120 mg; 0.882 mmol) and 10 % palladium carbon (160 mg) were charged, and the resultant mixture was stirred at 50° C. under a hydrogen pressure of 80 kg/cm2 for 12 hours. After cooling, the reaction mixture was filtered to separate palladium carbon, admixed with water and extracted with n-hexane. The extract was washed with saturated sodium hydrogen carbonate solution, dried and concentrated to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (172 mg; 0.796 mmol).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customto separate palladium carbon
  4. extractionextracted with n-hexane
  5. washThe extract was washed with saturated sodium hydrogen carbonate solution
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6ab9a66b767c4d15b892762e87b57d36
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767882

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