Print out/paste the table of contents or outline view from a PDF

Looking for some help, not such a power user as a I would like!

I want to be able to index/outline/create a table of contents for big PDF files, that I can paste or print.

I review large PDF files (Medical records), in Preview or PDF Expert, and use both Catalina on desktop and iPad at times. Sometime someone else has even indexed the records to create a table of contents, but what I would really like to do is be able to make a table of contents to paste into my report (word), or print. I mainly use the macOS for screen space, but would use an iPad solution if needed.

In PDF expert for Mac I can make an Outline/Table of contents, but no way to print/paste the outline/TOC. I tried asking their support site, they say no.

Is there another way to do this? Different app? I own devonthink but so far have mainly used to OCR large PDF files for searching. Something like scrivener or ulysses- don’t have these but would be willing if they can do what I need.

(Huge bonus-maybe another topic- is generating a timeline from the dates of the significant records)


(edited to add that the table of contents does not have to link back to the original PDF once exported-I just need it as a list of documents reviewed that I then annotate- allows chronologic order of documents reviewed in the file, and a smaller compressed form of the record review. (so one large PDF file with TOC as my source, and then also the TOC headings to be able to export to a word doc)

Probably theoretically possible, but it appears none of the commercial products have this (based on you asking “PDF Expert”. I assume you checked Adobe?

I found How to print table of contents of a pdf? - Unix & Linux Stack Exchange which gives some ideas. Maybe in your organisation you can find some programmers who could take this on as a project and also interrogate the files for the timelines you want. If the info is in the files and a pattern can be discerned, then they may be able to do it. Probably not easy.

I haven’t tried it, but you might have a look at muPDF.

Another options would be to highlight (possibly using a different color) the elements you want to be in the TOC, then export those highlights to markdown (etc.) which you could format as needed.

There just doesn’t seem to be a good way to do this (unless muPDF can).

There seems to be a possible round about way using MarginNote and PDFExpert on the iPad.

  • import document to MarginNote
  • create note links for table of contents
  • export note links as Word to PDFExpert
  • convert Word to PDF
  • append original document to converted note file
  • remake all of the table of content links to the pages of interest

This is a messy operation at best.


Thanks I looked at the Stack exchange thing and it is way beyond my level. Thanks.

That’s what was sort of behind my suggestion for you to seek help from your organisation. Hopefully the opportunity is big enough to attract some internal funding. Yes, it probably is complicated and difficult; hence commercial app’s have not gotten there yet.

On Mac I use a small app called PDF Outliner (you can buy it directly from the developer or from App Store) that not only does a fantastic job editing/creating PDFs’ table of contents, but also allows me to copy paste them to any document. Maybe it will work for you.


Looks promising…nice catch.

I’m an academic and so need it for my reading notes. This app is a true little gem.

Thanks-Will check out MarginNote.

Once I copy the table of contents out to paste it into my word doc, it does not have to link back to the huge original document.
The former table of contents becomes a much more compact, tight list of the dates and events, and I paste screen shots or type in additional info as a section in a report I write.

Oh wow! This is great!

I could do this on the command-line using the Stack Exchange link, but I think for $5 I would recommend this app instead. That’s a good price for a little utility like this.

The ability to generate a TOC is well worth the price itself. I’ve made some of those by hand and it usually takes ages. This took seconds.

I like that you can also buy it directly (I usually prefer to avoid the Mac App Store), but I went ahead and purchased their ‎PDF Believer Pack for $15 that looks like it would be useful, and then I don’t have to worry about installation limits that some apps that are sold via Paddle have.

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Coming across this TOC issue myself, but willing to grin and bear it. The I looked at that PDF Believer Pack and the combination of PDFOutliner, PDFExplode, and PDFoo (f it works, I’ve had bad luck with links into PDFs before) looks easily worth the $15, so I bought. I’m referencing multi-hundred page technical books every day, most without functioning TOCs so will see how this works before the day is out!

Adding that the author of these also has a free app PDFCombo that merges PDFs together. I’ve always just used Preview for that, but PDFCombo creates a new TOC with all the TOCs of the documents merged in. And I’m still trying to figure out these tools, especially PDFoo.

Thanks for the tip. Just tried it out. The automatic generation of TOC doesn’t look fantastic. From what I understand, the automatic generation is based on the font traits (size, font) of titles and subtitles. When the differences between them are small, the autoTOC is a mess. But it’s quite print-friendly tho.

You can control the autoTOC a bit. Check it here (video): PDFOutliner 1.5 Released on Mac App Store - onekerato

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This looks like it will solve my issue- will play with it. Thanks so very much!!!
The fact that you can copy the TOC items is the huge solution.

Appreciate your help!

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Yeah, I first read the instruction and then tested my own document (a thesis without clickable TOC). Probably because of the problem of the document itself, e.g., no font differences between the second-level heading and the third-level heading, the final generated TOC wasn’t so good.

Depending on that (font differences and AutoTOC reliability), I sometimes spend more time fixing TOCs. More rarely I do the TOCs non-automatically, using the sibling/child insertion.

Nonetheless, I find PDF Outliner super-valuable in my PDFs workflow.

Another option is PDFsam basic from

The free version allows you (amongst other things) to merge separate pdfs into one document, create bookmarks for each document in the merger and adds a hyperlinked, paginated table of contents as a front page.

The front page is just a pdf page, so you can then extract it from the pdf as a standalone document or …

There are other functions as well which I have not used.

Between preview and PDF expert, I can mark and combine and read PDF massive files pretty well…PDF expert has stamps I can use when going back thru the file, and I can make a TOC, but it killed me that that TOC was only within that file. Just the ability in PDF outliner to copy and paste the TOC to another doc is great. Funny how something so seemingly simple is not a feature. Annotations can be printed out in PDF expert, but show up in a weird format, that might have been my back up plan.