Water → 3,3-Dimethylhex-5-en-2-one

HRID 359142Notes

Reaction equation

HRID 359142 reaction equation
Br[CH2:2][CH:3]=[CH2:4].CC(C)[C:7](=[O:9])[CH3:8].[OH-].[K+].O.[C:14]1(C)[CH:19]=CC=C[CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:2][C:3]([CH3:4])([C:7](=[O:9])[CH3:8])[CH2:19][CH:14]=[CH2:15]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 7841Allyl bromideHCID 112513-Methyl-2-butanoneHCID 14797Potassium Hydroxide

Product 1

HCID 126041733,3-Dimethylhex-5-en-2-oneYield 31.7%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 121 g (1.0 mol) of 3-bromopropene and 103 g (1.2 mol) of 3-methyl-2-butanone is added dropwise during the course of 2 hours to a suspension of 168 g (3.0 mol) of potassium hydroxide powder and 10 g of tetrabutylammonium bromide in 300 ml of toluene with stirring. During this addition, the reaction temperature is kept below 30° C. The reaction mixture is kept at room temperature for a further 2 hours, then mixed with water, and the organic phase is separated. The organic phase is washed twice with water, dried and distilled through a packed column at ambient pressure. 40 g (31.7% of theory) of 4,4-dimethyl-1-hexen-5-one are obtained as a clear liquid of boiling point 151°-154° C.

Workup

  1. additionDuring this addition
  2. customis kept below 30° C
  3. customthe organic phase is separated
  4. washThe organic phase is washed twice with water
  5. customdried
  6. distillationdistilled through a packed column at ambient pressure

Sources & evidence

ORD record
ord-640f499eb33743c08433df63ab791a60
Source dataset
uspto-grants-1991_03
Patent number
US04999440

Reaction notes

Loading…