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I have a bunch of PDF files named, say, chapter1, chapter2, etc. I would like to combine them into a single file and create a table of contents where each file gets an entry.

If memory serves, there used to be a tool called CombinePDFs that could do that, but it was written as a RealBASIC application and does not seem to work on OS X 10.8 anymore.

Any alternative suggestion?

Note: it's really about the automatic table of contents feature; I know how to merge/join/combine PDF files without one.

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How should the individual chapters be named (where does the name come from)? – patrix Dec 20 '12 at 17:16
The filename would do perfectly. – Fr. Dec 21 '12 at 10:26
up vote 7 down vote accepted

PDFCombo, new free app for Mac OS X, combines PDFs and preserves the table of contents. It can also add a TOC entry based on filename to link to first page of every contributing PDF in the combined PDF.

Download here:

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Fits exactly the job, works exactly as advertised. Thanks. – Fr. Oct 29 '13 at 11:16

PDF Pen Pro 6 is my weapon of choice for this sort of advanced processing task.

I find in PDF handling software on the Mac, you generally get what you pay for. This is premium software for advanced tasks and scripting. Their lighter version might suit your two needs as well, so check before buying.

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Same observation here, you get what you pay for, no free tool surpasses PDFpenPro. I have version 5.8.5 that combines PDF files through the AppleScript menu, anything new in version 6? And most importantly, does it create a TOC for the final result? – Fr. May 30 '13 at 15:16

If you use the 'Combine / Merge to single PDF option in Acrobat Pro 9' this makes one PDF where the TOC has an entry for each file.

Unfortunately this is not freeware.

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Easiest/Most expensive. – Fr. May 30 '13 at 15:17

Calibre appears to be a freeware solution that you could use to break down these PDFs into files that you could use inside iBA, which would allow you to create a ToC with the newly added files and export the final product as a PDF. Definitely more time consuming than the method mentioned for Acrobat, but less expensive.

Calibre E-Book Management

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Unfortunately, the amount of combining I have to do requires an automated solution for generating the TOC. – Fr. May 30 '13 at 15:17

PDFOutliner is available in the Mac App Store and works great for me when I need to create or edit a Table of Contents. I want to note that this application does not appear to be a good solution for combining the PDF documents. But once they are combined -- perhaps with some of the free solutions mentioned here -- this very inexpensive app does a good job of managing the ToC.

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For those who don't know the first merge step, open both in Preview. Then drag on PDF icon on top of the other ones. More details here. It doesn't require additonal software.

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And how does this create a table of contents? – patrix Dec 20 '12 at 17:15
I'm pretty sure it does not, given the comments at the link. – Fr. Dec 20 '12 at 17:17

You can start by using preview's "INSERT" option.

Start by opening pdf(1), then click on "EDIT" then "INSERT" (pdf2) from file.

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The question asks for combining PDFs and creating a new table of content. Can you elaborate on the TOC part as well? – patrix May 30 '13 at 8:15

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