Hydrochloric Acid → 3-Chloro-2-hydroxy-4-methoxy-2'-trifluoromethylbenzophenone

HRID 652907Notes

Reaction equation

HRID 652907 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[C:4]=1[Cl:11].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].Cl>ClCCCl>[Cl:11][C:4]1[C:3]([OH:2])=[C:10]([CH:9]=[CH:8][C:5]=1[O:6][CH3:7])[C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]([F:12])([F:23])[F:24])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 130157172-Chloro-1,3-dimethoxybenzene

Product 1

HCID 140125683-Chloro-2-hydroxy-4-methoxy-2'-trifluoromethylbenzophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1.7 g of 2-chlororesorcinol dimethyl ether and 2.08 g of o-trifluoromethyl benzoyl chloride in 50 ml of 1,2-dichloroethane at 5°-7° C., 1.6 g of ferric chloride is added gradually. The mixture is brought to room temperature and allowed to stand 18 hours. The reaction mixture is refluxed 30 minutes and poured into 5% HCl and ice. The aqueous phase is extracted with additional organic solvent. The combined organic extracts are washed with water, dried over Na2SO4 and evaporated to give 3-chloro-2-hydroxy-4-methoxy-2'-trifluoromethylbenzophenone, mp 101°-102° C.

Workup

  1. customis brought to room temperature
  2. temperatureThe reaction mixture is refluxed 30 minutes
  3. extractionThe aqueous phase is extracted with additional organic solvent
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-2e7699a6b65c43ffa16b18d6d6e9ef58
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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