Ethyl Acetate → Propylene glycol methyl ether acetate

Temperature

70 °C

30 g of poly(p-hydroxystyrene) (VP8000) produced by Nippon Soda Co., Ltd. was dissolved in 120 mL of dimethylsulfoxide (DMSO), and 2.21 g of 1-chloromethylnaphthalene, 34.51 g of potassium carbonate and 0.56 g of sodium iodide were added thereto. The mixture was stirred at 70° C. for 4 hours, and the reaction solution was returned to room temperature. Thereafter, 100 mL of ethyl acetate and 100 mL of distilled water were added thereto, and 130 g of an aqueous 23% acetic acid solution was little by little added to the reaction solution while stirring the reaction solution in ice water. The reaction solution was transferred to a separating funnel, and 100 mL of ethyl acetate and 100 mL of distilled water were further added. After stirring, the aqueous layer was removed, and the organic layer was washed with 200 mL of distilled water five times. The organic layer was then concentrated and dissolved in 120 g of tetrahydrofuran (THF). Thereto, 26.53 g of triethylamine was added, and the reaction solution was cooled to 0° C. Furthermore, 23.43 g of the 3-chloro-3-benzyloxypropionitrile solution above was added dropwise, and the reaction solution was returned to room temperature and then stirred for 4 hours. After adding 200 ml of distilled water to the reaction solution, THF was removed by an evaporator, and 200 mL of ethyl acetate was added to the residue. The reaction solution was transferred to a separating funnel, and the aqueous layer was removed. The organic layer was washed with 200 ml of distilled water three times, concentrated to about 150 mL by an evaporator and added dropwise in 2 L of hexane. A part of the obtained precipitate was sampled for NMR measurement, and the remaining was dissolved in 75 g of PGMEA. From the obtained solution, the low boiling point solvent was removed by an evaporator to obtain 105.2 g of a PGMEA solution (29.6 mass %) of Resin (P-22).

1. customwas returned to room temperature
2. additionby little added to the reaction solution
3. customThe reaction solution was transferred to a separating funnel
4. stirringAfter stirring
5. customthe aqueous layer was removed
6. washthe organic layer was washed with 200 mL of distilled water five times
7. concentrationThe organic layer was then concentrated
8. dissolutiondissolved in 120 g of tetrahydrofuran (THF)
9. additionThereto, 26.53 g of triethylamine was added
10. temperaturethe reaction solution was cooled to 0° C
11. additionFurthermore, 23.43 g of the 3-chloro-3-benzyloxypropionitrile solution above was added dropwise
12. customwas returned to room temperature
13. stirringstirred for 4 hours
14. additionAfter adding 200 ml of distilled water to the reaction solution, THF
15. customwas removed by an evaporator, and 200 mL of ethyl acetate
16. additionwas added to the residue
17. customThe reaction solution was transferred to a separating funnel
18. customthe aqueous layer was removed
19. washThe organic layer was washed with 200 ml of distilled water three times
20. concentrationconcentrated to about 150 mL by an evaporator
21. additionadded dropwise in 2 L of hexane
22. aliquotA part of the obtained precipitate was sampled for NMR measurement
23. dissolutionthe remaining was dissolved in 75 g of PGMEA
24. customFrom the obtained solution, the low boiling point solvent was removed by an evaporator

ORD record

ord-c9be835da54b4c9387a0badb38c4dc0f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735048B2