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

HRID 895682Notes

Reaction equation

HRID 895682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[Al+3].[Cl-].[Cl-].[Cl-]>[C]=S>[Cl:9][CH2:10][CH2:11][C:12]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:8])[CH:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 72382-ChlorotolueneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 223809733-Chloro-1-(4-chloro-3-methylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 178503046HCID 178503046, compoundSolvent2×

Procedure

23.43 ml of 2-chlorotoluene and 26.6 g of 3-chloropropionyl chloride are mixed in 25 ml of carbon sulfide and 32 g of AlCl3 in 125 ml of carbon sulfide are added over 45 minutes. After stirring for 3 hours at RT, the solvent is evaporated and then 1 liter of water is added. The reaction medium is extracted with ether and then with benzene, and then the organic phase is washed with a saturated Na2CO3 solution and then with water. It is dried over Na2SO4 and then the residue is chromatographed on a silica column, eluting with an AcOEt/cyclohexane (5/95; v/v) mixture. 27.25 g of the expected compound are obtained.

Workup

  1. customthe solvent is evaporated
  2. addition1 liter of water is added
  3. extractionThe reaction medium is extracted with ether
  4. washwith benzene, and then the organic phase is washed with a saturated Na2CO3 solution
  5. dry with materialIt is dried over Na2SO4
  6. customthe residue is chromatographed on a silica column
  7. washeluting with an AcOEt/cyclohexane (5/95; v/v) mixture

Sources & evidence

ORD record
ord-4826ff1f2d9b4330a43fc6984ef2d2ff
Source dataset
uspto-grants-2005_07
Patent number
US06916838B1

Reaction notes

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