Potassium Carbonate → Ethylene glycol di(1-hydroxyethyl) ether

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.

1. customThe thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g
2. customReaction
3. customreaction
4. waitwas carried out for a further 2 hours at room temperature
5. customreaction
6. waitwas carried out for 6 hours at 60° C
7. customfollowed by separation
8. washThe ethyl acetate layer was washed twice with 300 g of water
9. concentrationconcentrated in vacuum
10. dissolutionThe residue was dissolved in 300 g of methanol
11. additionadded dropwise to 20 liters of water whereupon a powdery solid
12. customprecipitated
13. filtrationThe solid was collected by filtration
14. washwashed with 20 liters of water
15. customdried in vacuum at 40° C. for 24 hours
16. additionthe carboxyl group moieties which had been introduced in an amount of 2.0 mol %

ORDレコード

ord-54ca99d415b8468ba478fc554115c79e

出典データセット

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06027854