4-(2,2-二氯乙烯基)苯酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 22 g (0.06 mole) of 3-(tetrahydropyranyloxy)-1-(2,2,2-trichloro-1-acetoxyethyl)-benzene were dissolved in 80 ml of glacial acetic acid, 4.6 g (0.07 mole) of zinc dust were added a little at a time, and the mixture was heated at 60°-70° C. for 3 hours. The mixture was cooled and filtered, after which it was introduced into 1.5 liters of water and extracted with ether. The extracts were combined, washed three times with NaHCO3 solution and water, dried end evaporated down, and the residue was taken up in toluene. The solution was filtered over silica gel, and 8.0 g of 4-dichlorovinylphenol were obtained as a wax-like product. the mixture was heated at 60°-70° C. for 3 hours The mixture was cooled filtered after which it was introduced into 1.5 liters of water extracted with ether washed three times with NaHCO3 solution and water dried end evaporated down The solution was filtered over silica gel

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 22 g (0.06 mole) of 3-(tetrahydropyranyloxy)-1-(2,2,2-trichloro-1-acetoxyethyl)-benzene were dissolved in 80 ml of glacial acetic acid, 4.6 g (0.07 mole) of zinc dust were added a little at a time, and the mixture was heated at 60°-70° C. for 3 hours. The mixture was cooled and filtered, after which it was introduced into 1.5 liters of water and extracted with ether. The extracts were combined, washed three times with NaHCO3 solution and water, dried end evaporated down, and the residue was taken up in toluene. The solution was filtered over silica gel, and 8.0 g of 4-dichlorovinylphenol were obtained as a wax-like product. the mixture was heated at 60°-70° C. for 3 hours The mixture was cooled filtered after which it was introduced into 1.5 liters of water extracted with ether washed three times with NaHCO3 solution and water dried end evaporated down The solution was filtered over silica gel

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In an autoclave were placed 0.5 g of p-hydroxy-β,β-dichlorostyrene ##STR12## 1.0 g of sodium hydroxide and 5 ml of methanol. The mixture was heated at 120°-130° C. for 4 hours. Then the methanol was distilled off. To the residue was added 10 ml of water and the mixture was refluxed for 30 minutes. After completion of the reaction, the reaction mixture was acidified by concentrated hydrochloric acid and was extracted three times with 10 ml of ether. The extract was dried over anhydrous magnesium sulfate and the ether was distilled off. The residue was purified by silica gel column chromatography by using benzene, n-hexane and ethyl acetate (10:10:3) as a developer solvent to afford 0.3 g of p-hydroxyphenylacetic acid ##STR13## Yield 94.5%, m.p. 151°-152° C. NMR (CDCl3, δ, ppm) 3.50 (s, 2H), 4.25 (b.s., 2H), 6.92 (m, 4H) The mixture was heated at 120°-130° C. for 4 hours Then the methanol was distilled off To the residue was added 10 ml of water the mixture was refluxed for 30 minutes After completion of the reaction was extracted three times with 10 ml of ether The extract was dried over anhydrous magnesium sulfate the ether was distilled off The residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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. a cathode chamber separated from each other by a diaphragm the reaction liquid from the cathode chamber 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 the residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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. a cathode chamber separated from each other by a diaphragm the reaction liquid from the cathode chamber 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 the residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 22 g (0.06 mole) of 3-(tetrahydropyranyloxy)-1-(2,2,2-trichloro-1-acetoxyethyl)-benzene were dissolved in 80 ml of glacial acetic acid, 4.6 g (0.07 mole) of zinc dust were added a little at a time, and the mixture was heated at 60°-70° C. for 3 hours. The mixture was cooled and filtered, after which it was introduced into 1.5 liters of water and extracted with ether. The extracts were combined, washed three times with NaHCO3 solution and water, dried end evaporated down, and the residue was taken up in toluene. The solution was filtered over silica gel, and 8.0 g of 4-dichlorovinylphenol were obtained as a wax-like product. the mixture was heated at 60°-70° C. for 3 hours The mixture was cooled filtered after which it was introduced into 1.5 liters of water extracted with ether washed three times with NaHCO3 solution and water dried end evaporated down The solution was filtered over silica gel

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In an autoclave were placed 0.5 g of p-hydroxy-β,β-dichlorostyrene ##STR12## 1.0 g of sodium hydroxide and 5 ml of methanol. The mixture was heated at 120°-130° C. for 4 hours. Then the methanol was distilled off. To the residue was added 10 ml of water and the mixture was refluxed for 30 minutes. After completion of the reaction, the reaction mixture was acidified by concentrated hydrochloric acid and was extracted three times with 10 ml of ether. The extract was dried over anhydrous magnesium sulfate and the ether was distilled off. The residue was purified by silica gel column chromatography by using benzene, n-hexane and ethyl acetate (10:10:3) as a developer solvent to afford 0.3 g of p-hydroxyphenylacetic acid ##STR13## Yield 94.5%, m.p. 151°-152° C. NMR (CDCl3, δ, ppm) 3.50 (s, 2H), 4.25 (b.s., 2H), 6.92 (m, 4H) The mixture was heated at 120°-130° C. for 4 hours Then the methanol was distilled off To the residue was added 10 ml of water the mixture was refluxed for 30 minutes After completion of the reaction was extracted three times with 10 ml of ether The extract was dried over anhydrous magnesium sulfate the ether was distilled off The residue was purified by silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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. a cathode chamber separated from each other by a diaphragm the reaction liquid from the cathode chamber 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 the residue was purified by silica gel column chromatography