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

HRID 1493061

Reaction equation

HRID 1493061 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 105421111-(2-Methoxy-3,4,6-trimethylphenyl)-1-phenyl-2-methylpropanolYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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-butyllitium (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.

Workup

  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

Sources & evidence

ORD record
ord-98369ab0a9f6401d9d8c5e79199e8cd7
Source dataset
uspto-grants-1994_12
Patent number
US05376681

Linked notes

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