Hydrochloric Acid → HCID 18915768, compound

HRID 725712Notes

Reaction equation

HRID 725712 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15]([O:17]C)[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:17][C:15]1[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=[C:11]([Cl:10])[C:16]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 815021-Chloro-3,5-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18915768HCID 18915768, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.1 g (100 mmol) of benzoyl chloride are added dropwise with stirring at room temperature to a solution of 19 g (110 mmol) of 1-chloro-3,5-dimethoxybenzene and 14.7 g (110 mmol) of AlCl3 in 100 ml of toluene. The mixture is held at 70° C. with stirring for 5 h. The reaction mixture is cooled, then treated with 10% HCl and extracted with toluene. The resulting solution is washed with water and subsequently with saturated sodium chloride solution. The residue which remains after drying over MgSO4, filtering and concentrating by evaporation is purified by chromatography over silica gel (ethyl acetate/hexane 1:5). The product is recrystallized from hexane. 13.9 g of the compound are obtained as pale yellow crystals having a melting point of 92°-94° C.

Workup

  1. customis held at 70° C.
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with toluene
  4. washThe resulting solution is washed with water and subsequently with saturated sodium chloride solution
  5. dry with materialafter drying over MgSO4
  6. filtrationfiltering
  7. concentrationconcentrating by evaporation
  8. customis purified by chromatography over silica gel (ethyl acetate/hexane 1:5)
  9. customThe product is recrystallized from hexane

Sources & evidence

ORD record
ord-70928aa8e828476aa161686325b4dd1e
Source dataset
uspto-grants-1998_01
Patent number
US05707690

Reaction notes

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