Sync iTunes library to USB flash drive?

I have a 160GB iPod Classic that I’ve been using to provide the music in my car. I maintain the library in iTunes on a PC and every now and again I unplug the iPod from the car, plug it in to the PC so it can sync any new music. This has worked very well as I’ve been able to search for and play music from the car controls and see the artwork and track information on the car’s screen.
The issue is I just got a new car (BMW X2 2020 model) and the iPod no longer works in it, apparently it will only now work with newer iPods with the lightning connector.
The dealer suggested exporting the iTunes library to a USB flash drive and assured me that would work. However while it looks simple enough to copy the entire library to a USB drive, I don’t want to do that every time I add music to the iTunes library, what I really want is to sync the flash drive to the iTunes library so that it only copies new music.
I use an Android phone but bluetooth is not an option as there’s not enough space on the phone for all the music I’d want to put on it, it is a 160GB iPod after all.
So what are my options, if any to be able to sync an iTunes library to a flash drive? Free is good but I don’t mind paying a modest fee for the right software if it will do exactly what I want.

Can you get an adapter that converts the old iPad fitting to the lightning conductor?

Something like this, all sorts of adapters are out there to connect one generation Apple to the next
Screenshot 2020-08-10 at 16.21.47

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I don’t think that will work, the USB port in the car is still regular USB. I suspect when the dealer said iPods with lightning connectors he meant recent devices and versions of IOS, it is probably the OS on the iPod Classic that is incompatible (I’m guessing here?).

Same principle, I must admit I have an 160 gb old style iPod and a five year old Mini, my Mini has a USB point and they work fine.

If it has a USB point I would hope it would connect, though I must admit the menu on my Mini is confusing (or maybe I’m just old)

Could be, the car has “CarPlay”? That directly interacts with recent iOS Versions, might be even “iPhone only”. (No Pads or Pods.)

Syncing the files over should be easy - on Linux and Mac I’ve used “rsync” (command line tool, though); not sure this is available for Windows.
You can also look at tools like FreeFileSync.

It’s just to copy changed/new files from the iTunes sub-folders to any (external) drive.

The iPod worked fine in my previous car (BMW X1 2017 model). When I plug it in to the USB socket it shows as connected on the iPod screen and the car screen recognises the name of the iPod but it just won’t let me browse or play anything. The new car has an updated version of the iDrive software that clearly doesn’t like the iPod classic OS

That FreeFileSync looks the business as long as the car will recognise the iTunes library folder correctly. I’ll need to test it out.

Proof if proof were needed that to really *ugger things up you need a computer.

I had the misfortune to spend a number of hours pre -lockdown at a BMW dealer. So many issues with computers.

Great believer in KISS (Keep it simple stupid) Don’t think BMW do themselves favours .

Proof also that latest isn’t always greatest

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There is the story of 50 Land Rover Defenders that arrived in Africa and which didn’t have any computer reliance

They went like hot cakes.

Don’t know if the story is correct

Easy option would be to buy a new iPod Touch or switch your Android phone to an iPhone. I think both options will work with Apple CarPlay, so making for a better interface, especially if going the iPhone route.

You won’t need the full library folder (with all meta-data and stuff), but there should be a Music folder or so with all the music below it. (Standard sorting: by artist, by album.)
That’s what you should copy.

A new iPod touch with sufficient capacity would be £300 and I’m not minded to do that. As for going the iPhone route, only when hell freezes over.

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I copied the top level iTunes folder on to an external drive and was able to browse in to the folder for each artist. However doing that I’m not able to search and the artwork for the album isn’t displayed.
I also tried using the external drive I use for my NAS backup with the music I use on the ND5XS2 all in FLAC format in a simple artist\album file structure. They play fine and display the album artwork as well as the track information from the metadata (rather than the file name) but again there’s no ability to search.
What a nuisance this is, surely it can’t have been too difficult for BMW to provide some backwards compatibility?

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A small sum compared to the cost of the car.

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It is looking like FreeFileSync to an external drive from my NAS is the best solution so far. Even that is not ideal; no search ability is annoying. Also, I don’t really need FLAC for the car as the system isn’t really good enough to tell the difference between FLAC and a decent mp3 or aac, all that means is that any external storage has to be bigger and more expensive than what I really need.

True, but it is still a decent chunk of cash.

It is the fact I have to spend more than I think is absolutely necessary rather than the amount. I am Scottish after all :rofl:


iTunes could convert your FLAC to AAC.
But unless it’s doing so while sync’ing to an iSomething device, it will create more files in the same folders.

Then you would have to remove the duplicates from the library again; don’t delete (or move) the files; and sync only the AACs to the disk.

Might be easier to search for a converter tool, which could also handle the sync in the same go…
… but I haven’t searched for anything like this yet.

No, I’d just stick with FLAC then I just have one library to worry about. But the lack of ability to search on an external drive really is a nuisance.