Triethylamine → HCID 88243341, compound

Participants

Reaction Steps

The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 30.0 g of triethylamine and then 2.0 g of diethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 35.0 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 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. 6) in which 18.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene 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 diethylene glycol di(1-hydroxyethyl) ether to provide crosslinking.

Provenance & Evidence