Although an iTunes playlist can be automatically synced to your iPod when it's connected to your computer, non-Apple MP3 players may not support the iTunes playlist. Whereas MP3 players released in the past two to three years provide support for the M4A iTunes file extensions, older MP3 players are limited to MP3 or WAV files. Songs that are unprotected, or free of Digital Rights Management, in your iTunes playlist can be converted into a WAV or MP3 file and transferred to your MP3 player.
Open the iTunes program on your computer.
Click "Edit" at the top of the iTunes window and click "Preferences" from the sub-menu. On Macintosh computers, click "iTunes" at the top of the screen and select "Preferences."
Click "Import Settings" and select "MP3 Encoder" or "WAV Encoder" from the drop-down menu at the top of the program window.
Click "OK" to save the configuration, and click "OK" on the main window to exit the iTunes preferences.
Click the playlist in the iTunes sidebar, and click the first song in the playlist. Press and hold the "Shift" key on your keyboard, and click the last track in the playlist to highlight the entire playlist.
Right-click the highlighted area, and click "Create MP3 (or WAV) Version." Alternatively, click "Advanced" at the top of the screen and select "Create MP3 (or WAV) Version" from the sub-menu.
Drag and drop the newly converted files to your desktop, and plug the MP3 player's USB cable into the connector port on the MP3 player and the USB port on the computer.
Double-click the "My Computer" icon on your desktop, and double-click the "Removable Disk" icon that represents the MP3 player. On your Macintosh computer, double-click the MP3 player icon on your desktop.
Drag the songs from the desktop and drop onto the Removable Disk window, and click the back arrow button at the top of the window to return to the My Computer window. On Macintosh computers, drag and drop the songs onto the MP3 player's window.
Right-click the "Removable Disk" icon, and click "Eject" on the pop-up menu to disconnect the MP3 player from your PC. Alternatively, drag the MP3 player icon to the Trash icon on your dock to disconnect the MP3 player.