Sulfuric Acid → p-Tetrahydropyranylstyrene p-hydroxystyrene

Participants

Reaction Steps

To a solution of poly(p-hydroxystyrene) (9.0 g) [MARUKA LYNCUR-M, manufactured by Maruzen Petrochemical Co., Ltd., Mw 10000 and Mn 5000] in dimethoxyethane (100 ml), 3,4-dihydro-2H-pyran (12.6 g) and conc. sulfuric acid (0.5 ml) were added, followed by reaction at 30°-40° C. for 15 hours with stirring. After reaction, the mixture was evaporated in vacuo, the residue was neutralized by addition of sodium carbonate and poured into H2O (1 liter). The precipitate was filtered by suction, washed with H2O and dried under reduced pressure to give 11.0 g of the title compound as a white powder having Mw 10000 (GPC with polystyrene calibration). The composition of the polymer was found to be p-tetrahydropyranyloxystyrene unit and p-hydroxystyrene unit in a molar ratio of ca. 3:7 based on 1HNMR.

Provenance & Evidence