DAE baby have trouble taking liquid meds?

I've been noticing it happening for my 3m old for a little while now everytime I give him gripe water or tylenol. I stopped giving him the gripe water and only gas drops, which he has no problem with. Tylenol as needed ofc. I just gave him some since he was inconsolable and has been drooling/eating his hands way too much. I'm thinking he's starting to teethe.

I did it as I'm supposed to, in the cheek and upright. He started to choke and I ran him to my husband. He's fine now but I'm not sure what's causing this?

Does anyone else's LO ever have trouble like this? It's making me so nervous.