Patent retrieval is a recall-oriented search task where the objective is to find all possible relevant documents. Queries in patent retrieval are typically very long since they take the form of a patent claim or even a full patent application in the case of prior-art patent search. Nevertheless, there is generally a significant mismatch between the query and the relevant documents, often leading to low retrieval effectiveness. Some previous work has tried to address this mismatch through the application of query expansion (QE) techniques which have generally showed effectiveness for many other retrieval tasks. However, results of QE on patent search have been found to be very disappointing. We present a review of previous investigations of QE in patent retrieval, and explore some of these techniques on a prior-art patent search task. In addition, a novel method for QE using automatically generated synonyms set is presented. While previous QE techniques fail to improve over baseline retrieval, our new approach show statistically better retrieval precision over the baseline, although not for recall. In addition, it proves to be significantly more efficient than existing techniques. An extensive analysis to the results is presented which seeks to better understand situations where these QE techniques succeed or fail.