1-chloro-1-ethoxyethane

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

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 39.0 g of triethylamine and then 1.7 g of ethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 23.2 g of 1-chloroethyl ethyl ether was added, and reaction was carried out for a further 2 hours at room temperature. To this, 10.2 g of potassium carbonate and then 6.7 g of tert-butyl chloroacetate were added and reaction was carried out for 6 hours at 60° C. After the reaction mixture was allowed to cool down to room temperature, 500 g of ethyl acetate and 300 g of water were added thereto, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 14) in which 24.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, 5.0 mol % were replaced by tert-butoxycarbonylmethyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of ethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature reaction was carried out for 6 hours at 60° C followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 49.5 g of triethylamine and then 1.9 g of 1,4-butane diol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 13.6 g of tert-butyl dicarbonate was added, and reaction was carried out for a further 2 hours at 40° C. After the reaction mixture was allowed to cool down, 23.2 g of 1-chloroethyl ethyl ether was added and reaction was carried out for 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 10) in which 24.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, 7.0 mol % were replaced by tert-butoxycarbonyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of 1,4-butane diol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at 40° C to cool down reaction was carried out for 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g, was dissolved in 180 g of tetra-hydrofuran. With stirring under ice cooling, 2.3 g of triethylene glycol divinyl ether and then 1.8 g of pyridinium p-toluenesulfonate were added. Reaction was carried out for 6 hours at room temperature, 46.5 g of triethylamine and then 30.0 g of 1-chloroethyl ethyl ether were added, and reaction was carried out for a further 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 5) in which 31.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, and the alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol % formed ether bonds with alcoholic hydroxyl groups of triethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 49.5 g of triethylamine and then 2. 4 g of triethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 30.0 g of 1-chloroethyl ethyl ether was added, and reaction was carried out for a further 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H--N MR analysis, it was identified to be a polymer in which 31.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of triethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. This polymer is designated Polym. 1 whose rational formula is shown at the end of Synthesis Examples. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

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

Procedure: To 4,5-dichloro-2-(3,4-dichlorophenyl)-pyrrole-3-carbonitrile (5.0 g, 0.016 mol) dissolved in 300 mL of tetrahydrofuran is added, portionwise, potassium t-butoxide (2.75 g, 0.025 mol) with ice cooling and stirring. The cooled mixture is treated with a solution of 1-chloroethyl ethyl ether (2.31 g, 0.021 mol) in 15 mL of tetrahydrofuran at 10° C. over a 5 minute period. The mixture is stirred for 1/2 hour at ambient temperatures, evaporated to a volume of 50 mL and poured into a mixture of 200 mL of ethyl acetate and 100 mL of water. The organic layer is separated, washed with water (2×100 mL), saturated NaCl solution (1×100 mL), dried over anhydrous magnesium sulfate and evaporated to give the title product 5.9 g, mp 124°-126° C. is added evaporated to a volume of 50 mL poured into a mixture of 200 mL of ethyl acetate and 100 mL of water The organic layer is separated washed with water (2×100 mL), saturated NaCl solution (1×100 mL) dried over anhydrous magnesium sulfate evaporated

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 39.0 g of triethylamine and then 1.7 g of ethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 23.2 g of 1-chloroethyl ethyl ether was added, and reaction was carried out for a further 2 hours at room temperature. To this, 10.2 g of potassium carbonate and then 6.7 g of tert-butyl chloroacetate were added and reaction was carried out for 6 hours at 60° C. After the reaction mixture was allowed to cool down to room temperature, 500 g of ethyl acetate and 300 g of water were added thereto, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 14) in which 24.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, 5.0 mol % were replaced by tert-butoxycarbonylmethyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of ethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature reaction was carried out for 6 hours at 60° C followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 49.5 g of triethylamine and then 1.9 g of 1,4-butane diol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 13.6 g of tert-butyl dicarbonate was added, and reaction was carried out for a further 2 hours at 40° C. After the reaction mixture was allowed to cool down, 23.2 g of 1-chloroethyl ethyl ether was added and reaction was carried out for 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 10) in which 24.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, 7.0 mol % were replaced by tert-butoxycarbonyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of 1,4-butane diol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at 40° C to cool down reaction was carried out for 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g, was dissolved in 180 g of tetra-hydrofuran. With stirring under ice cooling, 2.3 g of triethylene glycol divinyl ether and then 1.8 g of pyridinium p-toluenesulfonate were added. Reaction was carried out for 6 hours at room temperature, 46.5 g of triethylamine and then 30.0 g of 1-chloroethyl ethyl ether were added, and reaction was carried out for a further 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 5) in which 31.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, and the alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol % formed ether bonds with alcoholic hydroxyl groups of triethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. The thus obtained partially hydroxypropylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the alcoholic hydroxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 49.5 g of triethylamine and then 2. 4 g of triethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 30.0 g of 1-chloroethyl ethyl ether was added, and reaction was carried out for a further 2 hours at room temperature. To the reaction mixture were added 500 g of ethyl acetate and 300 g of water, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H--N MR analysis, it was identified to be a polymer in which 31.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by 1-ethoxyethyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of triethylene glycol di(1-hydroxyethyl) ether to provide crosslinking. This polymer is designated Polym. 1 whose rational formula is shown at the end of Synthesis Examples. The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g Reaction reaction was carried out for a further 2 hours at room temperature followed by separation The ethyl acetate layer was washed twice with 300 g of water concentrated in vacuum The residue was dissolved in 300 g of methanol added dropwise to 20 liters of water whereupon a powdery solid precipitated The solid was collected by filtration washed with 20 liters of water dried in vacuum at 40° C. for 24 hours the carboxyl group moieties which had been introduced in an amount of 2.0 mol %

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

Procedure: To 4,5-dichloro-2-(3,4-dichlorophenyl)-pyrrole-3-carbonitrile (5.0 g, 0.016 mol) dissolved in 300 mL of tetrahydrofuran is added, portionwise, potassium t-butoxide (2.75 g, 0.025 mol) with ice cooling and stirring. The cooled mixture is treated with a solution of 1-chloroethyl ethyl ether (2.31 g, 0.021 mol) in 15 mL of tetrahydrofuran at 10° C. over a 5 minute period. The mixture is stirred for 1/2 hour at ambient temperatures, evaporated to a volume of 50 mL and poured into a mixture of 200 mL of ethyl acetate and 100 mL of water. The organic layer is separated, washed with water (2×100 mL), saturated NaCl solution (1×100 mL), dried over anhydrous magnesium sulfate and evaporated to give the title product 5.9 g, mp 124°-126° C. is added evaporated to a volume of 50 mL poured into a mixture of 200 mL of ethyl acetate and 100 mL of water The organic layer is separated washed with water (2×100 mL), saturated NaCl solution (1×100 mL) dried over anhydrous magnesium sulfate evaporated