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Tetraethylammonium → 2,2,2-Trichloro-1-(4-methoxyphenyl)ethan-1-ol

HRID 463902
Notes
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Reaction equation

HRID 463902 reaction equation
C([N+](CC)(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C)C=O.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1.[C:36](Cl)([Cl:39])([Cl:38])[Cl:37]>C(Cl)(Cl)Cl>[Cl:37][C:36]([CH:32]([C:31]1[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=1)[OH:33])([Cl:39])[Cl:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5413TetraethylammoniumHCID 5943Carbon TetrachlorideHCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 51779312,2,2-Trichloro-1-(4-methoxyphenyl)ethan-1-olYield 94.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 10 g quantity of tetraethyl ammonium salt of p-toluenesulfonic acid was dissolved in 60 ml of dimethylformamide containing 0.1 mole of chloroform. The solution was placed in a cathode chamber and in an anode chamber. Further 13.6 g (0.1 mole) of p-methoxybenzaldehyde and 0.01 mole of carbon tetrachloride was introduced into the cathode chamber. A glass filter was used as a diaphragm. Electrolysis was conducted at a constant current of 0.1 A. After current (2 F/mole) was passed, the reaction liquid was withdrawn from the cathode chamber. The carbon tetrachloride and chloroform were distilled off and the residue was extracted with methylene chloride. The methylene chloride was distilled off from the extract and the residue was distilled in a vacuum, giving trichloromethyl-4-methoxyphenyl carbinol. Yield 94.5%, b.p. 122°-124° C./1 mmHg.

Workup

  1. filtrationA glass filter
  2. customthe reaction liquid
  3. customwas withdrawn from the cathode chamber
  4. distillationThe carbon tetrachloride and chloroform were distilled off
  5. extractionthe residue was extracted with methylene chloride
  6. distillationThe methylene chloride was distilled off from the
  7. extractionextract
  8. distillationthe residue was distilled in a vacuum

Sources & evidence

ORD record
ord-f3ca9098886c4333bebe04fee96957f2
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04544766

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes