2-Chlorotoluene → 1-(4-Chloro-3-methylphenyl)propan-1-one

HRID 582916Notes

Reaction equation

HRID 582916 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:9][C:8]=1[CH3:13]

Participants

5

Reactant 3

HCID 72382-ChlorotolueneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 391041011-(4-Chloro-3-methylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
130 °C

Procedure

16 g of propionyl chloride are added dropwise to a mixture of 18 ml of o-chlorotoluene and 22.7 g of aluminum chloride and the reaction mixture is then heated at 130° C. for 3 hours. After cooling to RT, it is poured into a mixture of 100 ml of concentrated HCl and ice, extracted with ether, the organic phase is washed with saturated NaHCO3 solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is distilled off under reduced pressure to give 20.7 g of the expected product which crystallizes. B.p.=95° C. under 5 Pa.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with ether
  3. washthe organic phase is washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. distillationThe residue is distilled off under reduced pressure

Sources & evidence

ORD record
ord-f576ac33b72d4152955154c05da567fc
Source dataset
uspto-grants-1999_07
Patent number
US05925768

Reaction notes

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