Hydrochloric Acid → 5-Ethyl-2-methoxy-4'-trifluoromethylbenzophenone

HRID 1391338Notes

Reaction equation

HRID 1391338 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:17])([F:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH3:19].Cl>ClCCl>[CH2:18]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[C:24]([CH:25]=1)[C:11]([C:10]1[CH:14]=[CH:15][C:7]([C:6]([F:17])([F:16])[F:5])=[CH:8][CH:9]=1)=[O:12])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 736901-Ethyl-4-methoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 213309645-Ethyl-2-methoxy-4'-trifluoromethylbenzophenoneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminium chloride (0.6 g, 0.004 mole) was stirred in dichloromethane (2 ml) and treated with 4-trifluoromethylbenzoyl chloride (1 g, 0.0048 mole) (ice-bath cooling) and then with 4-ethylanisole (0.6 g, 0.0044 mole) in dichloromethane (1 ml). The mixture was stirred at room temperature overnight and then poured into ice and concentrated hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 10% NaHCO3 solution (100 ml), dried (MgSO4), filtered and evaporated to leave 5-ethyl-2-methoxy-4'-trifluoromethylbenzophenone (1.2 g) as a yellow oil. The latter was heated in 55% aqueous hydrogen bromide (27.5 ml) at 110°-120° C. for 5 hours. The mixture was evaporated to dryness to leave the required product.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution was washed with 10% NaHCO3 solution (100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-19b9f76e796a4b278719148d0a15ce32
Source dataset
uspto-grants-1979_02
Patent number
US04141995

Reaction notes

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