use Regexp::Assemble;
use List::Util qw(reduce);

# XXX why have a hash if its values are not used?
my @keys = map { quotemeta } keys %hash;

my $key_re = Regexp::Assemble->new->add(@keys)->re;

for my $string (@strings)
{
    my $match =
      reduce { length($a) > length($b) ? $a : $b }
      ($string =~ /\b($key_re)\b/gi);

    print "Found '$match' in '$string'\n"
      if defined $match;
}

[download]

Update1: Now handles multiple keys in same string.

Update2: Overlapping keys are not handled well, due to the left-to-right nature of the regex match. If this assumption can be made, hopefully this approach can improve performance. YMMV.

In reply to Re: Matching Many Strings against a Large List of Hash Keys (case insensitively, longest key first) by repellent
in thread Matching Many Strings against a Large List of Hash Keys (case insensitively, longest key first) by Anonymous Monk

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