Isopropanol → 4,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 915177

Reaktionsgleichung

Reaktionsgleichung von HRID 915177
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C([OH:17])(C)C>C(O)(=O)C.O.[O-2].[Cr+6].[O-2].[O-2]>[O:17]=[C:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4]1

Komponenten

6

Edukt 2

HCID 3776IsopropanolHCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 134632674,4,6-Trimethyl-1,2,3,4-tetrahydronaphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of chromium(VI)oxide (86 g, 0.861 mol) in acetic acid (400 mL) and water (40 mL) was added dropwise to a stirred solution of 1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalene in acetic acid (70 mL) and the reaction mixture stirred 2.5 hours at room temperature. Isopropanol (5 mL) was added and the whole concentrated in vacuo. The residue was dissolved in hexane and filtered over celite. The organic was washed with water and brine, dried (Mg2SO4), filtered and evaporated to give 40.3 g of 1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene and used without further purification in the bromination (step e). 1H NMR (300 MHz; CDCl3): 1.36 (s, 6 H), 1.98 (t, J=6.9 Hz, 2 H), 2.38 (s, 3 H), 2.68 (t, J=6.9 Hz, 2 H), 7.01 (dd, J1=0.6 Hz, J2=7.9 Hz, 1 H), 7.19 (d, J=0.6 Hz, 1 H), 7.90 (d, J=8.1 Hz, 1 H).

Aufarbeitung

  1. concentrationthe whole concentrated in vacuo
  2. dissolutionThe residue was dissolved in hexane
  3. filtrationfiltered over celite
  4. washThe organic was washed with water and brine
  5. dry with materialdried (Mg2SO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-11e0bfe9a35f4fc2ae2fb760a3fc6a06
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265139B2

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