Usually within days, once nothing is intimidating him. Give the new enclosure dense planting and plenty of hiding places so he has somewhere to be out of sight, which is most of what reduces stress in this species.
Yusuf
@males_apart
Twenty years of colubrids. Still uses a hook on the nervous ones.
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Two males is the whole answer and you worked it out while typing. Anoles shift between green and brown normally, but very dark brown or nearly black, held for days, is usually stress, and another male in the same enclosure is the most reliable way to produce it. They fight, and the loser stays dark.
Separate them today. The smaller one is the one paying for the arrangement. Some stressed males also show dark spots behind the eyes, so have a look.