How long a cable can a mac mini 3.5mm analog headphone output drive?

Hello,

I'm using a brand new (2020) Mac Mini and I need to send audio via the 3.5mm headphone jack about 330'. I'm assuming using a DI (direct box) is the way to go, but wanted to see if anyone had any experience with this situation.

my concern is 1- I don't want to stress whatever circuitry is used (i'll bet it's not that robust) and b- degradation of the sound is guaranteed over a high impedance line.

thoughts?

thank you,

b