[neobenzene]

Hi..I got this question on a test yesterday; I got up to a certain point after which I didn't know what to do.

The question : Convert methyl bromide to 2-methoxy propane

I know methyl bromide is CH3Br and 2-methoxy propane is CH3-CH(OCH3)-CH3

This is what I did

1) React CH3Br with CHCNa (Sodium ethynide) to form propyne
2) Hydrogenate propyne with a nickel catalyst (Propyne + 2H2) to form propane (CH3-CH2-CH3)
3) Now I want to add a methoxy group (OCH3) to the carbon #2. How do I do that?

But before that, is this sequence of steps correct?

[discodermolide]

You should not have hydrogenated it all the way to an alkane. There are plenty of methods that will stop it at the alkene level.
So find such a method and see where you can go from there.

[neobenzene]

Ok..so instead of adding 2H2, I'll add H2 in the presence of nickel to give me propene.

[discodermolide]

No that will do a complete hydrogenation. Try a Lindlar catalyst.
When you get to propene what's next?

[neobenzene]

I'm not sure

[discodermolide]

Try consulting a textbook or google it!

[neobenzene]

Can you give me a hint, if that's possible?

[discodermolide]

Have a look here:
http://books.google.ch/books?id=3fkEv6TDqpkC&pg=PA76&lpg=PA76&dq=synthesis+of+isopropanol&source=bl&ots=YCtyP2PVXc&sig=_ICHdxGHIZ-5Q-4hh5iR5cjU690&hl=en&sa=X&ei=p357UOmVDq714QSb6oDwAg&ved=0CDYQ6AEwAg#v=onepage&q=synthesis%20of%20isopropanol&f=false

[neobenzene]

So, if I add H2SO4 to propene, I will get (CH3)2-CH-O-SO3H. If I hydrolyse that, I will get CH3-CHOH-CH3

So all I need to do is to replace the "H" in the "OH" by a "CH3" group. Do I do Friedel Craft's alkylation?

[discodermolide]

No you do a Williamson's ether synthesis.

[neobenzene]

Thank you!