Toluene → 3,3-Dimethylhex-5-en-2-one

HRID 1789065Notes

Reaction equation

HRID 1789065 reaction equation
[OH-].[K+].[CH2:3](Cl)[CH:4]=[CH2:5].C([C:10]([CH3:12])=[O:11])(C)C.[C:13]1(C)[CH:18]=CC=C[CH:14]=1>[Cl-].C([NH+](CCCCCCCC)CCCCCCCC)CCCCCCC>[CH3:3][C:4]([CH3:5])([C:10](=[O:11])[CH3:12])[CH2:18][CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7850Allyl chlorideHCID 112513-Methyl-2-butanoneHCID 14797Potassium Hydroxide

Product 1

HCID 126041733,3-Dimethylhex-5-en-2-oneYield 76%

Reagents, catalysts & solvents 1

HCID 709151188-95-0Catalyst

Conditions

Temperature
70 °C

Procedure

63.6 g (1 mol) of powdered technical grade potassium hydroxide (88% strength) are suspended in 200 ml of toluene, and 10 g of trioctylammonium chloride are added. A mixture of 76.5 g (1 mol) of allyl chloride and 129 g (1.5 mols) of methyl isopropyl ketone is then added dropwise so that the temperature does not exceed 70° C. The mixture is stirred for a further 4 hours at 70° C., and is worked up as in Example 1. 96 g (76% of theory) of 4,4-dimethylhex-1-en-5-one of the abovementioned boiling point are obtained.

Workup

  1. additionis then added dropwise so that the temperature
  2. customdoes not exceed 70° C

Sources & evidence

ORD record
ord-51cb3e7d23ad4c4bb41ea2033ba73586
Source dataset
uspto-grants-1987_08
Patent number
US04686291

Reaction notes

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