:O

Woah. I just had the most unexpectedly wonderful email.

Recently I asked a professor about this weird reagent system for an undergrad experiment (bascially there's this reagent that seems absolutely useless, but the lab instructor doesn't know anything about it because he's a "substitute", so I hunted up a professor and asked). Anyway, the professor offered some suggestions, told me to look up the original prep, and then we went our separate ways.

Today he sent me references. Woah. (Also, oooooh.)

[Edited]
Maybe I should explain some details.

The reaction, is, I think, pretty standard: hydrolysis of dichlorodiphenylsilane to form the corresponding diol. Literally, you just need water, solvent, and the silane. Some people also add base (among other reasons, this removes the HCl byproduct and helps shift the reaction completely to the desired product side). What's weird is that my procedure tells me to add an alcohol. A somewhat bulky, aliphatic alcohol. Admittedly, alcohols won't attack the product much - alcoholysis of silanols is really slow, and the alcohol is bulky anyway - but won't the alcohol attack the dichlorodiphenylsilane?

What the professor I asked said was that the alcohol either 1. optimizes the solvent system so the product crashes completely out of solution once formed, or 2. as a "phase transfer catalyst-like" species that helps move water (from the obviously aqueous phase) into the organic layer (where the silane resides).

The references are procedures using the same set of reagents to make the product. Unfortunately, the authors didn't bother to explain themselves. And they used so much of the stuff, too! (Seriously, since when is it normal to use more than twice as much alcohol as solvent?)