Propranolol hydrochloride was synthesized from α-naphthol, epoxy chloropropane and isopropylamine via a serial of reactions included etherification, eliminate, ammoniation and salt formation. Then, its two derivatives, O-acetyl propranolol hydrochloride (compound 4) and polyacrylic acid immobilized propranolol hydrochloride (compound 7), were prepared by the reaction of propranolol hydrochloride with acetyl chloride and polypropylene chloride, respectively. Their structures were characterized by melting point, IR, 1H-NMR, and single-crystal X-ray diffraction analysis. The hydrolysis results under acidic conditions indicated that the releasing rate of propranolol hydrochloride in compounds 4 and 7 within 8 h was 15.18% and 17.86%, respectively. Compared with compound 4, the polymeric carrier of compound 7 is not easy to be absorbed by the body and can be expected as prodrug for clinical application.