1,2-Dichloroethane → Ethanone, 1-(4-methoxyphenyl)-2-[3-(trifluoromethyl)phenyl]-

HRID 1709000Notes

Reaction equation

HRID 1709000 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].ClCCCl.[F:17][C:18]([F:30])([F:29])[C:19]1[CH:20]=[C:21]([CH2:25][C:26](Cl)=[O:27])[CH:22]=[CH:23][CH:24]=1>O>[F:17][C:18]([F:29])([F:30])[C:19]1[CH:20]=[C:21]([CH2:25][C:26]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)=[O:27])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 127516363-(Trifluoromethyl)phenylacetyl chloride

Product 1

HCID 19073195Ethanone, 1-(4-methoxyphenyl)-2-[3-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anisole (32.4 g) and aluminium trichloride (36.0 g) are added to 1,2-dichloroethane (240 ml). The mixture is cooled to -5° and (3-trifluoromethylphenyl)-acetyl chloride (66.8 g) is slowly added. The mixture is stirred for 11/2 hours and poured into a mixture of crushed ice (400 g) and water (150 ml). After heating to room temperature, the compound is extracted with ether (3×200 ml). The combined organic phases are washed with a 2% aqueous solution of sodium hydroxide (200 ml and with water (3×200 ml), dried over magnesium sulphate and the solvents are removed invacuo. The residue is recrystallised from hexane. The product is dried in vacuo to constant weight to yield 2-(3-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethanone, m.p. 94°-95°.

Workup

  1. temperatureThe mixture is cooled to -5°
  2. extractionthe compound is extracted with ether (3×200 ml)
  3. washThe combined organic phases are washed with a 2% aqueous solution of sodium hydroxide (200 ml
  4. dry with materialwith water (3×200 ml), dried over magnesium sulphate
  5. customthe solvents are removed invacuo
  6. customThe residue is recrystallised from hexane
  7. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-11c54a752696410faea8ae03bbe44981
Source dataset
uspto-grants-1990_08
Patent number
US04946861

Reaction notes

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