Sulfuric Acid → 1-Chloro-4-[2,2,2-trichloro-1-(4-chlorophenoxy)ethyl]benzene

HRID 1658978Notes

Reaction equation

HRID 1658978 reaction equation
[Cl:1][C:2]([Cl:13])([Cl:12])[CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=1.S(=O)(=O)(O)O>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([O:11][CH:3]([C:2]([Cl:1])([Cl:12])[Cl:13])[C:4]2[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 46844-ChlorophenolHCID 214174-Chloro-alpha-(trichloromethyl)benzenemethanol

Product 1

HCID 215268891-Chloro-4-[2,2,2-trichloro-1-(4-chlorophenoxy)ethyl]benzene

Procedure

α-trichloromethyl-p-chlorobenzyl alcohol, 5.0g, was stirred with p-chlorophenol, 2.6g, and sulfuric acid, 35 ml, was added dropwise. After 2 hrs. of stirring, the mixture was poured onto ice and extracted with ether. After drying with sodium sulfate, the ether was removed under vacuum and the residue was recrystallized from ethanol to give α-trichloromethyl-p-chlorobenzyl p-chlorophenyl ether, mp 101°C. This method of synthesis is referred to in Table I as method A.

Workup

  1. additionwas added dropwise
  2. additionthe mixture was poured onto ice
  3. extractionextracted with ether
  4. dry with materialAfter drying with sodium sulfate
  5. customthe ether was removed under vacuum
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-606723cb101542fcac09f8013b72e1f1
Source dataset
uspto-grants-1976_06
Patent number
US03966824

Reaction notes

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