Isobutyrophenone → 1-(2-Methoxy-3,4,6-trimethylphenyl)-1-phenyl-2-methylpropanol

HRID 234270

Reaktionsgleichung

Reaktionsgleichung von HRID 234270
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[O:11][CH3:12].C([Li])CCC.[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH:19]([CH3:21])[CH3:20]>O1CCCC1.O>[CH3:12][O:11][C:3]1[C:4]([CH3:10])=[C:5]([CH3:9])[CH:6]=[C:7]([CH3:8])[C:2]=1[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:22])[CH:19]([CH3:21])[CH3:20]

Komponenten

6

Edukt 3

HCID 69144IsobutyrophenoneHCID 219613102-Bromo-3,5,6-trimethylanisoleHCID 178418339Butyllithium

Produkt 1

HCID 105421111-(2-Methoxy-3,4,6-trimethylphenyl)-1-phenyl-2-methylpropanolAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2-bromo-3,5,6-trimethylanisole (3.0 g, 13.1 mmol) in tetrahydrofuran (20 ml) was cooled to -78° C. and n-butyllithium (1.6M solution in hexane, 8.2 ml, 13.1 mmol) was added dropwise. The reaction mixture was stirred at the same temperature for 15 minutes. Then a solution of isobutyrylbenzene (1.94 g, 13.1 mmol) in tetrahydrofuran (5 ml) was added dropwise and the resulting mixture was stirred at room temperature for additional 30 minutes. The reaction mixture was diluted with water and the product was extracted with isopropyl ether. The extract was washed with water, dried and then concentrated. The residue was crystallized from hexane to obtain the desired compound (3.13 g, yield: 80.2%), m.p. 80°-81° C.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for additional 30 minutes
  2. extractionthe product was extracted with isopropyl ether
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-0e405f99f24a454c906ef7056abc014c
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594154

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