Toluene → HCID 12591156, compound

HRID 1789066Notes

Reaction equation

HRID 1789066 reaction equation
[OH-].[K+].[CH2:3](Br)[C:4]#[CH:5].C([C:10]([CH3:12])=[O:11])(C)C.[C:13]1(C)[CH:18]=CC=C[CH:14]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:3][C:4]([CH3:5])([C:10](=[O:11])[CH3:12])[CH2:18][C:13]#[CH:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 112513-Methyl-2-butanoneHCID 14797Potassium Hydroxide

Product 1

HCID 12591156HCID 12591156, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
45 °C

Procedure

70 g (1.1 mols) of powdered technical grade potassium hydroxide (88% strength) and 10 g of tetrabutylammonium bromide in 250 ml of toluene are initially introduced. A mixture if 119 g (1 mol) of propargyl bromide and 103.2 g (1.2 mols) of methyl isopropyl ketone is then added dropwise so that the temperature does not exceed 45° C. The mixture is stirred for a further 12 hours at 45° C., and is worked up according to Example 1. 67 g (54% of theory) of 4,4-dimethyl-hex-1-in-5-one of boiling point 55° C./12 mbar are obtained.

Workup

  1. customdoes not exceed 45° C

Sources & evidence

ORD record
ord-9a4daa9ae65a4e5fadbc80d78186f469
Source dataset
uspto-grants-1987_08
Patent number
US04686291

Reaction notes

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