2-Methyl-5-(p-tolyl)-3-pentanol → 1,1,7-Trimethyl-1,2,3,4-tetrahydronaphthalene

HRID 915178

Reaktionsgleichung

Reaktionsgleichung von HRID 915178
[CH3:1][CH:2]([CH:4](O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH3:3]>ClCCl>[CH3:1][C:2]1([CH3:3])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Komponenten

3

Edukt 1

HCID 617499612-Methyl-5-(p-tolyl)-3-pentanol

Produkt 1

HCID 2263961,1,7-Trimethyl-1,2,3,4-tetrahydronaphthaleneAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2-methyl-5-(p-tolyl)-3-pentanol (74 g, 0.385 mol) in dichloromethane (100 mL) was mixed with polyphosphoric acid (570 g) and the reaction mixture was heated to 60° C. and stirred overnight. After cooling, ice/water was slowly added and the aqueous extracted with dichloromethane. The organic layer was successively washed with water, aq NaHCO4, water and brine, dried (Mg2SO4), filtered and evaporated to give 67 g of 1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalene and used without further purification in the next step (step f). 1H NMR (300 MHz; CDCl3): 1.34 (s, 6 H), 1.69 (m, 2 H), 1.83 (m, 2 H), 2.37 (s, 3 H), 2.78 (m, 2 H), 6.99 (m, 2 H), 7.19 (s, 1 H).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe aqueous extracted with dichloromethane
  3. washThe organic layer was successively washed with water, aq NaHCO4, water and brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d3acbfcaa3714177bf120a6b757e0fab
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265139B2

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