Acetonitrile → p-METHYLACETOPHENONE

HRID 431308Notes

Reaction equation

HRID 431308 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9](#N)[CH3:10].[Li].C1C[O:16]CC1>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]([CH3:10])=[O:16])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 78104-ChlorotolueneHCID 8028TetrahydrofuranHCID 3028194Lithium

Product 1

HCID 8500p-METHYLACETOPHENONEYield 99%

Procedure

A mixture of 126.5 g (1 mol) of p-chlorotoluene and 45.1 g (1.1 mol) of acetonitrile (freshly distilled) is added dropwise to a suspension of 13.8 g (2.0 mol) of lithium granules in 350 ml of THF at −50° C. over the course of 2 hours. After a conversion determined by GC (the dark color of the reaction mixture prevents quantification of lithium consumption) of >98% (overall 7.5 h), the reaction mixture is added to 200 g of water, the pH adjusted to 2.0 using 37% HCl and the reaction mixture boiled for two hours under reflux. The organic phase is then separated off and the aqueous phase extracted once more with 100 ml of petroleum ether. The united organic phases are distilled. 132.7 g (0.99 mol) of 4-methylacetophenone (99%, boiling point 88° C./8 Torr) are obtained as a colorless liquid, GC purity >98% a/a, which when left to stand at RT gradually solidifies.

Workup

  1. distillationfreshly distilled)
  2. customquantification of lithium consumption) of >98% (overall 7.5 h)
  3. additionthe reaction mixture is added to 200 g of water
  4. temperatureunder reflux
  5. customThe organic phase is then separated off
  6. extractionthe aqueous phase extracted once more with 100 ml of petroleum ether
  7. distillationThe united organic phases are distilled

Sources & evidence

ORD record
ord-c19acb3ef232482a97e7bb235907460a
Source dataset
uspto-grants-2003_12
Patent number
US06657093B2

Reaction notes

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