http://macs.about.com/od/ipod/a/copy_via_ipod.htmNow that you have the songs you need from the Mac on the iPod, your next step is to copy the songs on to your PC. The ability to copy songs from your iPod back on to your Mac or PC is not supported in iTunes. Fortunately there are many third-party applications available that enable you to do this. See Copying Songs from Your iPod to a Mac or PC for a list of Mac and Windows utilities.
Download and install the utility of your choice. For instructional purposes the example below uses PodUtil. Make sure you read the accompanying PodUtil help file before you begin.
To copy songs from your iPod to your Windows PC:
1. Connect your iPod to your PC
2. Make sure disk mode is enabled. To check this, go to iTunes – Edit – Preferences – iPod and make sure the Enable disk use option is checked (grayed out is OK)
3. Open PodUtil
4. You will be presented with a window displaying your playlists on the left, the music in the selected playlist on the right, a Playing box on the bottom left and settings for copying on the bottom right
5. Click to select the songs you want to copy
6. Click on the Choose... button at the bottom and choose the folder to which your music will be copied
7. Click on the Copy Settings... button to choose how PodUtil copies your music. If the Sort by Artist and Sort by Album boxes are checked, PodUtil will organize the copied files by Artist and Album. If you have iTunes 4.5 or later you can have PodUtil add the copied songs to iTunes and rebuild your playlists
8. Click on the OK button
9. Click on the Copy button and PodUtil will copy the selected songs over to your PC. If you enabled the Add Songs to iTunes option it will add your songs to iTunes at the end.
Good luck!