[bimmer3]

I used a mixture of procedures, but it was basically oxidation of the alcohol with KMnO₄ while keeping it cool enough so the ketone would be produced. Then the addition of NaOH and benzaldehyde. Then added 1-propanol with more NaOH, a lot of NaOH was used because I didn't have a concentrated form on hand, just a diluted form. It was about equal amount of reagents except with an excess of NaOH.

[discodermolide]

Archer's suggestion is certainly viable.
However, with excess NaOH I think the hemiacetal will just reverse back to the ketone.
As I said with the information you have provided it is nearly impossible to suggest a reasonable structure for any product you have isolated.

[bimmer3]

understandable, what would be the most reasonable product using this sort of synthesis and what quantities of reagents (approx) would have to be used.  Would it be the 2,5-dibenzalcyclopentanone?

[bimmer3]

Or what would be a good next step after the 2,5-dibenzalcyclopentanone

[discodermolide]

What product are you aiming to get? The hemi-acetal? Because you will probably not be able to make that.

[bimmer3]

I think I am just going to stop at the 2,5-dibenzalcyclopentanone and boil off the other products.

[discodermolide]

If that is indeed the product. Try and find its melting or boiling point from the literature.

[bimmer3]

http://www.guidechem.com/dictionary/895-80-7.html

[Archer]

2,5-dibenzalcyclopentanone

The correct nomenclature is 2,5-dibenzylidenecyclopentanone

What is it exactly that you are trying to achieve in this series of experiments?

[discodermolide]

So it is a solid. See if you can get anything to crystallise.

[bimmer3]

It was supposed to be a synthesis project, but what I was looking to achieve would not be ideal, so seems like I am having to adjust.

[Archer]

Archer's suggestion is certainly viable.
However, with excess NaOH I think the hemiacetal will just reverse back to the ketone.

I agree, I have never seen a hemiacetal made in this way unless it was part of a cyclysation reaction.

[Archer]

It was supposed to be a synthesis project, but what I was looking to achieve would not be ideal, so seems like I am having to adjust.

What is the point in your synthesis project though? does this molecule have an application or are you just playing with the reagents at your disposal?

[discodermolide]

It was supposed to be a synthesis project, but what I was looking to achieve would not be ideal, so seems like I am having to adjust.

This is not a synthesis project it is alchemy.

[bimmer3]

pretty much playing with reagents at my disposal.