Hydrochloric Acid → Phenol, 4-(2,2-dichloroethenyl)-

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-hydroxyphenyl trichloromethyl carbinol ##STR6## 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 1.80 g of p-hydroxy-β,β-dichlorostyrene ##STR7## Yield 95.2%, m.p. 90°-91° C. IR (cm-1) 3370, 1604, 1500, 1442, 1375, 1235, 1180, 1109, 909, 873, 821, 682.

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

ORD record

ord-940e57a83357473c904f523c36bf5794

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04544766