4-Vinylphenol → 4-Ethynylphenol

Participants

Reaction Steps

To a solution of poly(p-hydroxystyrene) (4.0 g) obtained in above (1) in dimethoxyethane (70 ml) in a pressure vessel, isobutyrene (60 g) and conc. sulfuric acid (0.3 ml) were added at -60° C. or lower, the mixture was brought to 45° C. for 1 hour with stirring, and then stirring was continued at room temperature for 22 hours. After reaction, the mixture was evaporated, the residue was neutralized by addition of sodium carbonate and poured into H2O. The precipitate was filtered by suction, washed with H2O and dried under reduced pressure to give 4.1 g of poly(p-tert-butoxystyrene-p-hydroxystyrene) as a white powder having Mw 10000 (GPC with polystyrene calibration). The composition of the polymer was found to be p-tert-butoxystyrene and p-hydroxystyrene in a molar ratio of ca. 1:1 based on 1HNMR analysis.

Provenance & Evidence