1,3,5-trichloro-2-(2-chloroethoxy)benzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: reacting the 2-(2,4,6-trichlorophenoxy)-ethanol with thionyl chloride in the presence of benzyl-trimethyl ammonium chloride in a ratio of 1:60 by weight at a temperature of from 50° C. to 80° C. in the presence of carbon tetrachloride as solvent to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; and of from 50° C. to 80° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: reacting the 2-(2,4,6-trichlorophenoxy)-ethanol with thionyl chloride in the presence of benzyl-trimethyl-ammonium chloride in a ratio of 1:60 by weight, at a temperature of from 50° C. to 80° C., in the presence of carbon tetrachloride as solvent to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: reacting the 2-(2,4,6-trichlorophenoxy)-ethanol with thionyl chloride in the presence of benzyltrimethyl ammonium chloride in a ration of 1:60 by weight at a temperature of from 50° C. to 80° C., in the presence of carbon tetrachloride as solvent to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; and of from 50° C. to 80° C.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1-liter glass reactor, which could withstand a pressure of 6 atmospheres, fitted with a stirrer, heating mantle and a pressure gauge, were added 270.8 g 2-(2,4,6-trichlorophenoxy) ethyl chloride and 350 g n-propyl amine. The mixture was slowly heated with stirring over a period of 8 hours at a temperature of 90° C. The initial pressure under these conditions was 3 atmospheres, which dropped during the reaction to about 2.2 atmospheres. The end of the reaction was determined by GLC. At the end of the reaction the mixture was cooled to 55° C., whereupon the pressure dropped to atmospheric. The excess n-propyl amine was distilled off and it could be recycled for use in a subsequent batch, until a bottom temperature of 85° C. was reached. At the end of the distillation the mixture was cooled to 40° C., 300 ml of a 20% hydrogen chloride solution and 1 g of an emulgator GAF RM-510 were added. The temperature rose to 70° C., the mixture was stirred for one hour at this temperature and the product precipitated as white crystals of the amine hydrochloride salt. The slurry is cooled to 40° C., filtered, re-slurried in 250 ml xylene and filtered again. This affords 312 g of white hydrochloride salt of N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethyl amine in 93% yield and purity of 96%-98%. Into a 1-liter glass reactor, which could withstand a pressure of 6 atmospheres, fitted with a stirrer heating mantle The mixture was slowly heated dropped during the reaction to about 2.2 atmospheres At the end of the reaction the mixture was cooled to 55° C., whereupon the pressure dropped to atmospheric The excess n-propyl amine was distilled off could be recycled for use in a subsequent batch, until a bottom temperature of 85° C. At the end of the distillation the mixture was cooled to 40° C. 300 ml of a 20% hydrogen chloride solution and 1 g of an emulgator GAF RM-510 were added rose to 70° C. the mixture was stirred for one hour at this temperature the product precipitated as white crystals of the amine hydrochloride salt The slurry is cooled to 40° C. filtered, re-slurried in 250 ml xylene filtered again

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a three-necked, round-bottom flask fitted with a stirrer, thermometer, reflux condenser and dropping funnel was added 250 g of 96% 2-(2,4,6-trichlorophenoxy) ethanol, 250 ml carbon tetrachloride and 4 g of benzyl-trimethyl-ammonium chloride. The mixture was heated to 55° C. and 146 g thionyl chloride was added dropwise over 1.5 hours. After the addition of the thionyl chloride the temperature of the reaction was slowly raised to 80° C. for a total reaction tme of 2.5 to 3 hours. The end of the reaction was determined by GLC. The mixture was cooled to 60° C. and water slowly added to decompose the excess thionyl chloride. The phases were separated and the organic phase was washed with a 10% sodium hydroxide solution until it reached a pH of 7. After an additional separation of the phases the organic phase was washed again with water. After a further separation of phases, the carbon tetrachloride was distilled off to yield an oil which slowly crystallized to form 257 g of 2-(2,4,6-trichlorophenoxy)-ethyl chloride in a purity of 96%-98% and yield of 98%. Into a three-necked, round-bottom flask fitted with a stirrer thermometer, reflux condenser was slowly raised to 80° C. for a total reaction tme of 2.5 to 3 hours The mixture was cooled to 60° C. The phases were separated the organic phase was washed with a 10% sodium hydroxide solution until it After an additional separation of the phases the organic phase was washed again with water After a further separation of phases the carbon tetrachloride was distilled off to yield an oil which slowly crystallized

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reacting the 2-(2,4,6-trichlorophenoxy)-ethanol with thionyl chloride in the presence of a catalytic amount of a tetra-alkyl ammonium halide at a temp. of from 30° C. to 100° C., optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10° C. to 50° C. or in the presence of urea at a temperature of from 20° C. to 55° C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20° C. to 150° C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine. of from 20° C. to 150° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10° C. to 50° C. or in the presence of urea at a temperature of from 20° C. to 55° C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20° C. to 150° C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine.