Hydrochloric Acid → HCID 73667365, compound

HRID 463904Notes

Reaction equation

HRID 463904 reaction equation
[ClH:1].C([N+]([CH2:9][CH3:10])(CC)CC)C.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14](S(O)(=O)=O)=[CH:13][CH:12]=1.[Cl-:22].C([NH+]([CH2:28][CH3:29])CC)C.[OH2:30]>C(O)C>[CH2:21]([O:30][C:29]1[CH:28]=[CH:13][C:12]([C:10]([Cl:22])=[CH:9][Cl:1])=[CH:11][CH:16]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 5413TetraethylammoniumHCID 6101p-Toluenesulfonic acidHCID 12698378Triethylazanium chloride

Product 1

HCID 73667365HCID 73667365, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10 ml quantity of concentrated hydrochloric acid, 2.5 g of tetraethyl ammonium salt of p-toluenesulfonic acid and 5.5 g of triethyl ammonium chloride were dissolved in 60 ml of ethanol. The solution was placed in an anode chamber and a cathode chamber separated from each other by a diaphragm. In the cathode chamber was further introduced 10 m mole of p-benzyloxyphenyl trichloromethyl carbinol ##STR4## Then constant-current electrolysis was performed with use of lead as a cathode and carbon as an anode. After current (5 F/mole) was passed, the reaction liquid from the cathode chamber was added to 200 ml of water. The mixture was extracted four times with 50 ml of hexane. Then the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography, giving 2.54 of p-benzyloxyphenyl-dichloroethylene ##STR5## Yield 91.0%, m.p. 74.5°-76.5° C.

Workup

  1. customa cathode chamber separated from each other by a diaphragm
  2. customthe reaction liquid from the cathode chamber
  3. extractionThe mixture was extracted four times with 50 ml of hexane
  4. dry with materialThen the extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0728c68dbb247d18e5c5238c9349e60
Source dataset
uspto-grants-1985_10
Patent number
US04544766

Reaction notes

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