Condense music on ipod that is no longer in my computer's library

Hi. So, I have had a 60gig ipod for God-knows-how-long now....pre2006 I think. Anyway, I hadn't realized that music was meant to flow only one way (computer to ipod and not vice versa), so I deleted much of my music library from my computer after transferring to my ipod. I have TONS of cds on there and have completely filled the ipod. I was hoping to just convert the larger files to MP3s, but this option in iTunes is greyed out when I have my ipod connected. (Obviously, I am not automatically syncing with my current library). Two questions:
1. MOST IMPORTANT: Is there a way to condense music files directly ON the ipod, when songs aren't in my computer's music library anymore?
2. What is the best option for backing up 60gig or more of music FROM my ipod & other locations & condensing it to the same place/library?
Thanks for your help!
erika

An iPod (especially an old one) is a very dangerous place to keep your only copy of song files. You should not do (1) at all, even if it is possible. (I can't think of a way to do it directly.)
There is no way to transfer music from iPod to computer using iTunes (except for songs you purchased from the iTunes Store). However, there are third-party methods and utilities for transferring from iPod to computer. If you do a Google search on something like "ipod transfer mac," you should get some links.
Once the song files are back on your Mac (and maybe even backed up to a second location), add them to your iTunes library. Now, you can use the Create AAC Version command in iTunes (menu bar under Advanced) to convert them to a "condensed" format. Note: The old files will still be there as well after converting.
In iTunes preferences General tab Import Settings, you can change the conversion options. I recommend using AAC Encoder at iTunes Plus. That creates 256 kbps AAC files (which is what the iTunes Store uses). If you want "MP3" files, you can select the MP3 Encoder there.
Then, you can sync your iPod to the converted song files. And you will have achieved what you wanted with (1), plus your valuable songs files are now backed up on your computer.

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Did you restore the iPod on this computer?
What exactly happens when you try to sync?
Does iTunes see the iPod?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
If so have you done anything like update iTunes on the computer since it last successfully synced?
Do the songs play in iTunes?
Does any media now sync to the iPod?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod
Try syncing using the manual method
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If you regained use of the iPod without restoring (doubtful, restoring will also update the iPod)) then do the following:
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If your having trouble syncing, come back and let us (fellow users) know.

Condense music on ipod that is no longer in my computer's library

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