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

HRID 620066Notes

Reaction equation

HRID 620066 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 in vacuo. 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 in vacuo
  6. customThe residue is recrystallised from hexane
  7. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-8f23000255814d37accaa0726927d36e
Source dataset
uspto-grants-1989_04
Patent number
US04818765

Reaction notes

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