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Sigil has many Table of Contents generation tools built in.
Is this an epub2 or an epub3?
If an epub 2, you can use the Create Table of Contents menu to fill the NCX.
If an epub3, it fills in the NAV.
There is also a Create HTML Table of Contents and fill it as well.
i never try to do this in Word.
See the sigil user guide for more info.
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