4‐Isopropenyl phenol (4‐IPP) is a versatile dual functional intermediate that can be prepared readily from bisphenol‐A (BPA). Through etherification with epichlorohydrin to the phenolic group of 4‐IPP, it can be converted into 4‐isopropenyl phenyl glycidyl ether (IPGE). On further reaction with carbon dioxide in the presence of tetra‐n‐butyl ammonium bromide (TBAB) as the catalyst, IPGE was transformed into 4‐isopropenylphenoxy propylene carbonate (IPPC) in 90% yield. Cationic polymerization of IPPC with strong acid such as trifluoromethanesulfonic acid or boron trifluoride diethyl etherate as the catalyst at −40 °C gave a linear poly(isopropenylphenoxy propylene carbonate), poly(IPPC), with multicyclic carbonate groups substituted uniformly at the side‐chains of the polymer. The cyclic carbonate groups of poly(IPPC) were further reacted with different aliphatic amines and diamines resulting in formation of polymers with hydroxy‐polyurethane on side‐chains. Syntheses, characterizations of poly(IPPC) and its conversion into hydroxy‐polyurethane crosslinked polymers were presented. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 802–808