[AlphaScent]

Dear all,

I have been given the task of synthesizing 3-hydroxy-2-hexanone (racemic).  The problem is I have never done this particular reaction using these exact conditions.

The reaction is 1-hexyn-3-ol with 1) Boron trifluoride etherate, Mercuric Oxide and methanol and then 2) 6 N HCl.

This is what the notes say:

HgO 6.0 g in 700 mL MeOH

My problem is there is no reference and the last chemist is now gone and his notes are clear on the the order or hoe the reaction is to be done.  I have some thoughts and want to know it you think this is correct.

This is obviously a variation of the markonikov oxymercuration (hydration) of a triple bond.  The absence of sulfuric acid is a bit different, but boron trifluoride is no slouch in the lewis acid department.

With there being no water to form the enol, how does this reaction proceed??

Once you add the alcohol, the notes say after 1 hour you add 6 N HCL

[AlphaScent]

I posted on accident:

The notes say

                 HgO 6 g in MeOH
11-12pm     BF3 etherate 112 mL
1225-1250   1-hexyn-3-ol
1:50-2:30    remove MeOH (1/2)
2:40           add 6 N HCl 300 mL

(I assume I woudl add the acid at 0 degrees)

Thanks for any advice

[AlphaScent]

Im an idiot. 

Methanol adds as water and then there is hydrolysis of the enol ether with 6 N HCl.