"That "2.3," if that's the iPod's software version, sounds like the 3rd gen iPod (touch wheel with four separate touch buttons that glow orange).
That iPod model was the first with the Dock Connector, but it was designed to be used with FireWire. It will not charge over USB, although it may connect for data syncing if the battery is in good shape and it is fully charged from using the power adapter.
For most reliable results, you should keep using it with the FireWire port on the new Mac. You can get one of these FireWire 800 to 400 adapters.
http://eshop.macsales.com/item/Other%20World%20Computing/FIR1369AD/
There is also a way to use it with USB, if you have a FireWire-based power adapter (the one that came with this model iPod). Please post back if you want more info. "
Excuse me butting in here, but this sounds as though this is the thing I have been looking for !!!
I have been using my daughters old iPod in the car, where it plays ok getting the power from the car, they battery is pretty much dead, but useable in the car.
My problem is that now I have a new iMac with Firewire 800 connections, so I find can't update or change the music on the 20Gig iPod because the cables don't fit, my old G5 had the Firewire 400 so I had no problems.
Will this adaptor allow me to charge up the iPod as I transfer and update my music, as the internal battery will only hold the charge for a very short time ?