Hydrochloric Acid → (3,4-Dimethoxyphenyl)[4-(trifluoromethyl)phenyl]methanone

HRID 404855Notes

Reaction equation

HRID 404855 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].[Sn](Cl)(Cl)(Cl)Cl.Cl>ClCCl>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[C:7]([C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 24287Tin tetrachlorideHCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 14297391(3,4-Dimethoxyphenyl)[4-(trifluoromethyl)phenyl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Trifluoromethylbenzoyl chloride (200 grams), 1,2-dimethoxybenzene (128 mL), and dichloromethane (1800 mL) were combined in a reaction flask under a nitrogen atmosphere. Tin (IV) chloride (168 mL) was added to the reaction mixture slowly drop-wise over 45 minutes. The reaction mixture was heated to reflux for 11 hours. It was subsequently cooled to room temperature and slowly poured into a mixture of 200 mL of hydrochloric acid and 1800 mL of ice water. The layers were phase separated. The organic layer was washed with 4 portions of water (1 L each) and then with 1.5 L of 20% saturated aqueous sodium hydroxide (w/v). The organic layer was dried over anhydrous sodium sulfate and then concentrated by rotary evaporation. The residue was recrystallized in 1 L of 15% ethyl acetate/85% hexanes. The crystalline solid was collected by vacuum filtration yielding 132 grams of 3,4-dimethoxy-4′-trifluoromethylbenzophenone. This material was not purified further but was used directly in the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 11 hours
  3. customseparated
  4. washThe organic layer was washed with 4 portions of water (1 L each)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was recrystallized in 1 L of 15% ethyl acetate/85% hexanes
  8. filtrationThe crystalline solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-f6eb29e2ecd4411a95ab59c055bd1ba9
Source dataset
uspto-grants-2014_06
Patent number
US08748634B2

Reaction notes

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