Water → 3,3-Dimethyl-4-phenylbutan-2-one

HRID 1789067Notes

Reaction equation

HRID 1789067 reaction equation
[CH:1]([C:4]([CH3:6])=[O:5])([CH3:3])[CH3:2].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:2][C:1]([CH3:3])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](=[O:5])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 112513-Methyl-2-butanoneHCID 14797Potassium Hydroxide

Product 1

HCID 836703,3-Dimethyl-4-phenylbutan-2-oneYield 47.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

516 g (6 mols) of methyl isopropyl ketone, 759 g (6 mols) of benzyl chloride and 60 g (0.186 mol) of tetrabutylammonium bromide are dissolved in 1 liter of toluene, and the solution is heated to 100° C. 420 g (7.49 mols) of powered potassium hydroxide are slowly metered in at this temperature. The reaction mixture is stirred for 12 hours at 100° C. and cooled, and 1.5 liters of water are added. The organic phase is separated off, dried over sodium sulphate and distilled fractionally. 507 g of 3,3-dimethyl-4-phenylbutan-2-one of boiling point 82° C./0.05 mbar are obtained.

Workup

  1. temperaturecooled
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled fractionally

Sources & evidence

ORD record
ord-0e9e073cc57d485fad6ab38501ccba80
Source dataset
uspto-grants-1987_08
Patent number
US04686291

Reaction notes

Loading…