According to a recently revealed regulatory filing, Google this month sold its 5 percent stake in struggling online service AOL, netting $283 million. The transaction is notable for two reasons. First, it places the overall value of AOL at about $5.6 billion. Second, it means Google has lost over $700 million on its investment: It purchased the stake in 2006 for $1 billion.

The sell-off is just one step in AOL's pending spinoff from Time Warner, ending one of the uglier merger attempts in corporate history. (Sorry, Mercedes/Chrysler.) AOL merged with Time Warner in 2001 and the combined company even changed its name, temporarily, to AOL Time Warner. But with AOL's fortunes tanking in recent years, Time Warner reasserted itself and began distancing itself from AOL. The spinoff is expected to happen later this year.

AOL posted a loss of $1.53 billion in 2009 but somehow managed a $82.7 million profit in the first quarter of 2009. Time Warner says that an independent AOL "would be free to focus on growing its web brands and services and its advertising business.