the password protected file MUST be converted into the hash using john's modules IOT successfully crack the password
#convert the password protected file to john's format
root@oco:~$ find / -iname *2john* -type f 2>/dev/null
root@oco:~$ ls /opt/john/*2john*
* display various tools John can use to convert password-protected file into a format that john can attack
* naming style “{format}2john”
root@oco:~$ pdf2john.pl private.pdf > pdf.hash
* this cmd creates a hash challenge of a password protected file
root@oco:~$ cat pdf.hash
private.pdf:$pdf$2*3*128*-1028*1*16*c1e77e30a0456552cb8a5327241559bd*32*3dc175eae491edc29b937e4fdbda766c00000000000000000000000000000000*32*6a1b5158d8d6dd9e8380f87b624da6cc936075fd41dc3c76acf2d90db62e4a27
root@oco:~$ john -wordlist=/usr/share/wordlists/rockyou.txt pdf.hash
* M4y0rM41w4r3 (private.pdf)