First read the two numerals.
CCXXXI = 100 + 100 + 10 + 10 + 10 + 1 = 231
MDCCCLII = 1000 + 500 + 300 + 50 + 2 = 1852
Break the second numeral into its landmark parts and use the distributive law:
231 × 1852 = 231 × (1000 + 800 + 50 + 2)
= 231 × 1000 + 231 × 800 + 231 × 50 + 231 × 2
= 231000 + 184800 + 11550 + 462
= 427812
Check: 231000 + 184800 = 415800; 415800 + 11550 = 427350; 427350 + 462 = 427812 ✓
Now try to write 427812 in Roman numerals. The largest Roman symbol is M = 1000, so you would need 427 M’s followed by DCCCXII. Later Romans got round this with a bar over a numeral to mean “times 1000”:
427812 = 427 thousands + 812
427 = CDXXVII, 812 = DCCCXII
so 427812 = C̄D̄X̄X̄V̄Ī Ī DCCCXII
Why it happens: this is the joke in the cartoon. Being asked to multiply CCXXXI by MDCCCLII really was about as pleasant as fighting a lion — not because the arithmetic is deep, but because the notation gives you no help. In Hindu numerals you would set out 231 × 1852 in columns and be done in a minute, because every carry is “ten of these make one of those”.