A novel and convenient synthetic method for the preparation of alpha,omega-bis(2,6-dimethylphenol)-poly(2,6-dimethyl-1,4-phenylene oxide) (PPO-2OH) oligomer in water is presented. It is based on the oxidative copolymerization of 2,6-dimethylphenol (DMP) and aromatic diols in the presence of Cu-ethylene diamine tetraacetic acid catalyst in water. It was found that the mole fraction of PPO-2OH in the product was affected by species of aromatic diols and mole ratio of DMP to aromatic diols. Species and concentration of surfactants were demonstrated to be significant factors that would influence molecular weight (M-n) and yield of PPO-2OH. The synthesized PPO-2OH was end-group modified with methacryloylchloride (MAC) to obtain dimethacryloyl chloride telechelic PPO (PPO-2MAC). The relationship between glass transition temperature (T-g) and M-n of PPO-2OH is in good agreement with the Flory-Fox equation. Thermal polymerized low-molecular-weight PPO-2MAC has a constant T-g at about 208 degrees C.