1-Chloro-4-(chloromethyl)benzene → HCID 20368385, compound

HRID 616639Notes

Reaction equation

HRID 616639 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC(CCl)=CC=1>ClCCCl>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([C:8]2[S:9][C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 15422638HCID 15422638, compound

Product 1

HCID 20368385HCID 20368385, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 200 ml. of 1,2-dichloroethane were added 10 g. (0.042 mole) of 3-phenyl-6-methoxybenzothiophene and 6.5 g. (0.042 mole) of 4-chlorobenzoyl chloride. The mixture was cooled to 0° C., and 5.73 g. of aluminum chloride were added. The mixture was stirred overnight, and an additional 10 percent of 4-chlorobenzyl chloride and aluminum chloride was added. The reaction mixture was maintained for approximately one hour, and ice then was added to the mixture. The resulting organic layer was separated from the aqueous, the aqueous layer was washed with chloroform which was then added to the organic layer. The organic layer was evaporated to dryness. To the resulting residue were added 250 ml. of methanol and 15 ml. of 5N sodium hydroxide. The mixture was refluxed for 40 minutes and then was evaporated. The residue was dissolved in ethyl acetate, and the ethyl acetate solution was washed successively with water and aqueous sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and evaporated to give the title compound, m.p. 115° C.

Workup

  1. temperatureThe reaction mixture was maintained for approximately one hour
  2. additionice then was added to the mixture
  3. customThe resulting organic layer was separated from the aqueous, the aqueous layer
  4. washwas washed with chloroform which
  5. additionwas then added to the organic layer
  6. customThe organic layer was evaporated to dryness
  7. additionTo the resulting residue were added 250 ml
  8. temperatureThe mixture was refluxed for 40 minutes
  9. customwas evaporated
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washthe ethyl acetate solution was washed successively with water and aqueous sodium chloride
  12. dry with materialThe organic layer was dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated

Sources & evidence

ORD record
ord-6962bbd4ee29463ca5d5fa74e148ac3e
Source dataset
uspto-grants-1978_02
Patent number
US04075227

Reaction notes

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