Triethylamine → Triethylene glycol di(1-hydroxyethyl) ether

참여 물질

반응 단계

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.

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