Today we're going to prepare NSL via the reaction between

iodide and phenol, using a strong base.

We'll also show you some tips on recycling reagents so, this becomes quite an economical process.

First we need to prepare sodium methoxide, our strong base.

Measure out 150 ml of methanol, it's important that the, methanol is dry and free from water.

Add the methanol into a flask equipped with a thermometer, and stir bar.

The thermometer is probably optional, but we wanted to track, the temperature changes.

Now, before anything else, set up a reflux condenser on, the flask.

Make sure that you're using cold water to circulate, as, you'll see, we'll need it.

Weigh out an 8 gram chunk of sodium metalin, make sure that it's free of any oil from the, storage container.

Cut this into 4 or 5 lumps.

Now, the sodium metalin is in the flask, which can fit, in the flask.

Don't cut into two, small portions as, otherwise the reaction could go too fast.

Now, quickly unstopper the flask and add all the sodium, metal.

Quickly replace the condenser on top of the flask.

You'll see the sodium react vigorously with the methanol and, bubble and produce a lot of hydrogen gas.

The temperature will rise fast.

And, within about 30 seconds, the methanol will start to reflux very strongly.

You can see why using a good condenser in cold, water is important.

The complete reaction of the sodium, takes about 20 minutes.

Towards the end the little pieces of sodium dance round, and round the flask together.

Until finally, there's nothing left.

Here's our sodium methanol.

In this oxide solution, allow this to cool down, to below 50 degrees C.

Now weigh out 32 grams of phenol.

This will normally, be a crystalline solid at room temperature.

But if it's, a hot day it may turn slushy like this.

Be careful not to spill any, because the odor is, difficult to remove.

Place the beaker of phenol into a warm water bath, and allow it to melt.

This will take about 10 minutes.

Here's our molten phenol with a few small crystals remaining.

Now, unstopper the reaction flask and add the liquid phenol, into the flask.

The temperature will increase by about 10 degrees C at, this point.

Now start up magnetic stirring.

Replace the reflux condenser, and, allow the mixture to cool to below 40 degrees C.

While this is going on, weigh out 50 grams of, methyl iodide.

This is about 25 mils of, liquid due to the high density.

When the temperature is below 40 degrees in the flask,

add the methyl iodide to the reaction mixture through the, top of the condenser.

You may see the methyl iodide starting to refluxes.

It has a lower boiling point than methanol.

At this point top up the water bath with some, more ice and make sure that the condenser water temperature,

is nice and cold.

Now, with stirring, heat the mixture until it refluxes continuously.

To start with this, will happen at a temperature of, about 62 degrees C.

But the temperature will slowly rise, to just below 70 degrees after a while.

Let the mixture reflux and stir for an hour and, a half.

At the end of this time, quickly change the set,

to a full distillation.

No need for a thermometer.

The aim now is to distill off as much of, the methanol in the reaction, flask as possible.

This takes a little while.

The temperature again will rise as more methanol comes off, the mixture.

About an hour in and we can see white sodium, salts precipitating in the reaction flask,

as the solvent distills, off.

This is about 80 mils so we're over half way, there now.

Temperature in the flask, is 80 degrees C.

Here we are at the end of the distillation, it, looks like a solid caked into the reaction flask.

Here's our distilled methanol, we'll save this and use this.

Allow the reaction flask to cool and then prepare 100, mils of water.

Swirl around to, dissolve as much as possible.

You'll already see two layers separating.

Pour the mixture into a separating funnel and then wash, the flask out with a further 50 mils of water.

Add this to the separating funnel.

First we'll separate the organic layer and then wash the, aqueous layer to make sure we've, got all our product.

Here's the bottom aqueous layer.

And our organic layer, separate this into a flask.

Now we will extract our aqueous layer with dichloromethane to, make sure we've got all the product out.

Pour the aqueous layer back into the separating funnel.

Then measure out 50 mils of dichloromethane.

Add this to the aqueous layer in the flask.

Pour this into the separating funnel.

And give the mixture a good shake.

Take care with, venting the mixture as you shake.

Allow the layers to separate completely.

Then separate off the bottom dichloromethane layer into the same, flask as contains the organic product from before.

Wash out the separating funnel and add our organic product.

And dichloromethane to the funnel.

We now need to wash, this to get rid of excess phenol.

Prepare a solution of 10 grams of sodium hydroxide in, 50 ml of water and 50 grams of ice.

This should result, in a cool solution.

Add this to the separating funnel and shake the mixture, well for a good minute, remembering to vent often.

Allow the layers to separate.

Note that this might take, a little while.

So be patient.

Then separate off the bottom dichloromethane layer.

Okay we're nearly there.

We now need to wash the, dichloromethane layer with water to remove any sodium hydroxide.

So put it back into a washed separating funnel.

And now add 50 mils of cold water to the, funnel.

Shake well and allow to separate once again.

See how our organic layer is now nice and clean, and colorless.

Separate the bottom organic layer one last time into a, flask.

And then use some anhydrous calcium chloride to dry it, thoroughly.

The final step now is, to remove the dichloromethane and, distill our product.

So drain the dichloromethane solution into a flask and set, up for simple distillation.

The dichloromethane comes off fairly quickly as it has a, boiling point a good 100 degrees, lower than the anisole.

Once the temperature rises about about 100 degrees C we, place the foil jacket on the still head and change, the receiving flask to collect our product.

A colorless liquid starts to distill above about 140 degrees, C.

The product distills quite rapidly, and the total distillation time, was around 45 minutes.

At the end there's not much left in the flask, just a tiny amount of yellow residue.

And here's our product, 17 grams of pure anisole.

This, represents a 53% yield on starting phenol, which is, about the same as the literature quotes.

What's really nice in this reaction is that we can, take the aqueous layer from the separation, neutralize it using, acid, then add persulfate solution, to get our iodine back.

Then we react this with the methanol we distilled in, some red phosphorus, and obtain methyl iodide again.

Beautiful recycling.

Thanks for watching.