m-Xylyl chloride → HCID 17884111, compound

HRID 1073060Notes

Reaction equation

HRID 1073060 reaction equation
[OH-:1].[Na+].[O-2].[Ca+2].[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][CH:6]([CH3:5])[C:13](=[O:1])[CH3:12]

Participants

6

Reactant 3

HCID 12102m-Xylyl chlorideHCID 14798Sodium HydroxideHCID 6850728Calciumoxide

Product 1

HCID 17884111HCID 17884111, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

256 g of methyl ethyl ketone, 80 g of powdered NaOH, 28 g of calcium oxide and 10 g of tetrabutylammonium bromide were warmed with stirring. 141 g of 3-methylbenzyl chloride were added dropwise in the course of 90 minutes at 70° C. The mixture was then boiled under reflux for 1 hour, cooled, filtered and washed with methyl ethyl ketone, and the filtrate was concentrated and distilled through a 30-cm long column containing steel helices. 86% pure 3-(3-methylbenzyl)-butanone was obtained at a boiling point of 80° C. at 0.4 mbar in 40% yield.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with methyl ethyl ketone
  5. concentrationthe filtrate was concentrated
  6. distillationdistilled through a 30-cm long column
  7. additioncontaining steel helices

Sources & evidence

ORD record
ord-1a106c5119bd4e02aafac2be814a42d2
Source dataset
uspto-grants-1990_11
Patent number
US04968668

Reaction notes

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