Hey, everyone. So in this example question, it says, beginning from phenol, determine the chemical steps needed to prepare the following compound. Alright. So, here we're starting with phenol and we're trying to make this diether. Well, if we think about reactions where we can go from an alcohol to an ether, we should think about the Williamson ether synthesis where we would use a strong base to deprotonate our OH group into a phenoxide ion in this case and then do an SN₂ reaction with an alkyl halide.

Now that could help us to make one ether, but here we have two ethers. So that tells me I need to find a way to get two OH groups onto this benzene that are ortho to each other. And we know that we can do that from what we've learned so far. But what we're going to do here is first oxidize my phenol into a quinone. So remember, we can oxidize it through the use of our strong oxidizing agent in the form of dichromate.

Right. So that'll oxidize this. Here goes our quinone, our ortho quinone. We can then reduce this. We could use tin(II) chloride over hydrochloric acid, and that changes it into hydroquinone.

Now that I have two OH groups, I can do Williamson ether synthesis twice. So what I could do here is, first, I can use a strong base. Let's say we use KOH, and then followed by an alkyl halide, we need two carbons. So the OH− would deprotonate this OH or the other one, making it O−, and then we do an SN₂ reaction hitting this carbon and kicking out the Br.

And we get our first ether. And then since we have another OH, we just do it again. Here, I decide to break them up into steps to show how each individual OH group is converted into an ether group. You could also say KOH two equivalents and then an alkyl halide two equivalents to say that it happens twice so that both OH groups are converted into ethers. So, doing that yet again gives us as our final answer, our diether.

So here goes the two ether groups that I've created. Right. So again, we're able to do this by remembering that a phenol can be oxidized into quinone, and then from there, reducing the quinone to hydroquinone, and then using a reaction we've seen in the past by changing an OH group into an ether group by way of the Williamson ether synthesis reaction.