I found myself in a bind with a PDF document that was 112 MB in size when I photo copied all my housing papers into PDF files and combined them into one pdf.
cd folder
convert *.JPG papers.pdf
The file was impossible to email or even display in Google Drive due to its sheer size. I have found a work around to make it happen. Open the PDF you want to downsize in the Preview Mac OS X application.
You'll notice that when you go to the file -> export option, you only have Reduce File Size. I tried this and it made my pdfs nearly unreadable and extremely fuzzy. So the trick is to copy the Reduce File Size.qfilter found in /System/Library/Filters to /Library/Filters.
cp /System/Library/Filters/Reduce\ File\ Size.qfilter /Library/filters/Reduce\ File\ Size \Better.qfilter
Make two copies of this file. Append Better to one and then Best to the other. We will change the Name String at the end, and the ImageSizeMin/Max values.
Better should look like this.
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>Domains</key>
<dict>
<key>Applications</key>
<true/>
<key>Printing</key>
<true/>
</dict>
<key>FilterData</key>
<dict>
<key>ColorSettings</key>
<dict>
<key>DocumentColorSettings</key>
<dict>
<key>CustomLHSCorrection</key>
<array>
<integer>8</integer>
<integer>8</integer>
<integer>8</integer>
</array>
</dict>
<key>ImageSettings</key>
<dict>
<key>Compression Quality</key>
<real>0.0</real>
<key>ImageCompression</key>
<string>ImageJPEGCompress</string>
<key>ImageScaleSettings</key>
<dict>
<key>ImageScaleFactor</key>
<real>0.5</real>
<key>ImageScaleInterpolate</key>
<true/>
<key>ImageSizeMax</key>
<integer>1508</integer>
<key>ImageSizeMin</key>
<integer>508</integer>
</dict>
</dict>
</dict>
</dict>
<key>FilterType</key>
<integer>1</integer>
<key>Name</key>
<string>Reduce File Size Better</string>
</dict>
</plist>
Best should look like this.
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>Domains</key>
<dict>
<key>Applications</key>
<true/>
<key>Printing</key>
<true/>
</dict>
<key>FilterData</key>
<dict>
<key>ColorSettings</key>
<dict>
<key>DocumentColorSettings</key>
<dict>
<key>CustomLHSCorrection</key>
<array>
<integer>8</integer>
<integer>8</integer>
<integer>8</integer>
</array>
</dict>
<key>ImageSettings</key>
<dict>
<key>Compression Quality</key>
<real>0.0</real>
<key>ImageCompression</key>
<string>ImageJPEGCompress</string>
<key>ImageScaleSettings</key>
<dict>
<key>ImageScaleFactor</key>
<real>0.75</real>
<key>ImageScaleInterpolate</key>
<true/>
<key>ImageSizeMax</key>
<integer>3508</integer>
<key>ImageSizeMin</key>
<integer>1028</integer>
</dict>
</dict>
</dict>
</dict>
<key>FilterType</key>
<integer>1</integer>
<key>Name</key>
<string>Reduce File Size Best</string>
</dict>
</plist>
After doing both of these modifications, it will now show up in your exports options. Better reduced my file size down to 7 MB and Best reduced my file size down to 22 MB.