I am debugging a problem with a HTTP 301 Permanent Redirect. After a quick test, it seems that Safari clears its cache of 301s when it is restarted, but Firefox does not.
To clear a permanent redirect, go to chrome://settings/clearBrowserData and from there only clearing "cached images and files" cleared the redirect.
Go to chrome://net-internals. On the right of the top red status bar, click on the down arrow ▼ to open the drop-down menu, and under the "Tools" group, choose "Clear cache".
As of version 48, this was the only thing that worked for me to clear a cached 301.