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Restore iTunes library from iPod
Here's how ot restore your iTunes library from your iPod
Apple doesn't make copying music off an iPod or iPhone easy - has something to do with their relationship with the music companies.
Apple stores the music on iPods in an invisible directory which you will need to access, here's how.
To access that directory, you have to set your iPod to be used in Disk Mode. You can do this in iTunes on your iPod's info page. (To get to the info page, connect your iPod to your PC, then select its icon from the source column on the left.) If iTunes asks you to sync again, select "Cancel." This is important, if you synch your iPod to an empty music library you will erase all the music currently on your iPod.
Then, from the computer's "Start" menu, choose "My Computer." When that window opens, select "Folder Options" from the "Tools" menu.
On the "View" tab of "Folder Options," scroll down and select the box next to "Show Hidden Files and Folders," then click the "OK" button to save your choice and close the window.
Now, back in the "My Computer" window, look for your iPod to show up as a hard drive (probably the E drive). Double-click on the iPod's icon to reveal its contents.
You're looking for a folder called "iPod_Control." Inside will be a folder called "Music." Drag the "Music" folder to your hard drive icon.
Once the copy is complete, open iTunes, and in the "Edit" menu, open the "Preferences" window. In the "Advanced" tab, click to choose "Keep iTunes Music folder organized."
This setting will cause iTunes to copy and organize any music you add to your iTunes library.
Last, from the iTunes "File" menu, choose "Add Folder to Library" and navigate to the "Music" folder you copied. Select the folder, click "OK" and you'll see the music being copied to the iTunes library.
Mac users can download a program such as Pod to Mac, which I found at www.podtomac.com. It's free and makes transferring some or all of your iPod/iPhone's music a snap. There's a free version for Windows there, too.