Time required to evolve advanced chromatophores in octopuses and squid? Do we have any idea how long it took primitive Coleoida to evolve from non-color changing organisms to color changing organisms? Granted, not all coleoidans can change color (vampire squids are good example), many of them do. (Coleoida is the subclass below Cephalopoda that includes all squid, cuttlefish and octopuses. Nautilus' are excluded.)

Here is a print screen from oneZoom.org.

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Coleoida include decapods and octopods, both of which have chromatphores, so their MRCA (which lived 330 millions years ago) probably did as well. Coleoida is a sister group to the nautiloids. They branched +400 millions years ago. Together they form the group of cephalopods. As nautiloids do not have chromatophores, the evolution of chromatophores probably occurred in between these two nodes (between MRCA of cephalopods and MRCA of coleoida). In other words, it occurred at some point during a period of about +70 millions years.