I found this in my PC
Replacing Dipstick seal without dropping pan
Go to a IH truck location and get the right orings 2 one big for around the big plug and a small one for the dip stick. also make sure you have a set of gripper clamps like doctors use or a needle nose vise-grips, to hold the brass part so you dont loose it inside the pan.
1 pull dip stick and the starter /yes you need the room so you dont drop the brass nut.
2. put the big oring on the clamp then grab the hole the dip sick goes in then back off the nut. check it as some have stripped the threads over tighting it trying to stop leak. if it is stripped then you got problems as it can only be replaced by dropping the pan. sorry i have not done it so no help there
3. very easy push the big brass in and cut the oring and get rid of the old. slip the new in it fits in a grove and then pull it back where it goes and thighten the not to just good not over tight so you stripp the nut.
good luck
If you don’t get the o-ring that needed. Buy a new tube of the good rtv. Pulled the starter & cleaned the side of the pan. I used needle nose vise-grips (as suggested), and pulled the nut off. Then moved the housing into the pan. Pulled the o-ring, cleaned the o-ring & housing, put rtv on the o-ring & the outside of the pan. Slid the housing back in place & replaced the nut. Sorry to post so long.