Convert DRM-Free Files to a Friendlier Format
Most portable media players handle formats beyond MP3. But a car CD player, home DVD player, or other straggling device may play MP3 files exclusively and be unable to handle other compressed audio files. As long as your songs aren't locked into a proprietary DRM format, use this tip to convert them into MP3 files.
In iTunes, choose Edit, Preferences. Click the Advanced tab, and then click the Importing tab within it. Confirm that MP3 Encoder is selected--and while you're there, raise the bit rate to a customized setting of 256 kbps to improve sound fidelity slightly
In Windows Media Player, the procedure is different in its details but produces a similar result. Right-click a song, and pick Send to, Windows Audio Converter. Change the file format from the format listed (probably WMP) to MP3, and boost the quality (that is, the audio bit rate) to 256 kbps. Click Next, and complete your instructions by pressing