Another route to 2-Chloroethanol

[MrSamosa]

While NBK's method of reacting Ethylene Glycol with Hydrogen Chloride seems to be a nice way to make relatively large batches of Chlorohydrin, I, like many others, do not have any decent lab equipment in which to perform this synthesis...so I have been in search of alternate, more easy methods.

In my search for such a method, I theorized that it may be possible to convert 1,2-Dichloroethane to 2-Chloroethanol, and it turns out that there is a way! If you look up information regarding 1,2-Dichloroethane's degradation in the environment, you will find that there is a bacteria-produced enzyme called Haloalkane Dehydrogenase.. What it does is cleave the bond between a Halogen and a Carbon as follows, with the example of 1,2-Dichloroethane:

Cl-C-C-Cl + H2O --(Haloalkane Dehydrogenase)--> Cl-C-C-OH + H2O

This is nice, but I do not like to do lab syntheses involving bacteria...it seems like there are far too many conditions to meet in order to get a decent yield.

The question now is, is there a way to Hydrolyse 1,2-Dichloroethane to form 2-Chloroethanol? I imagine the problem with this would be to cleave just one Chlorine instead of both.

The advantage of this method would be that 1,2-Dichloroethane is extremely easy to find as a paint solvent, and the synthesis hopefully would not involve any special lab equipment...but that is just a "hopefully." :)

Sorry, I was trying to edit my post but missed, I don't think I changed anything...

[Mr Cool]

Since the reactants are paint stripper and water, obtaining a high yield can be sacrificed in favour of keeping it simple.
Thus, reflux for a while, then fractionally distil for purity. Quick `n` easy :).
Oh, but since you have water and a non-polar, reaction rate will be quite slow. Worse than that, the chlorohydrin will be significantly more water soluble than the dichloroethane, thus when formed it will be more likely to react further than dichloroethane.
Certainly I know that hydrolysis (perhaps in slightly alkaline conditions) of haloalkanes will take place, even though they are immiscible. This is shown by adding some silver nitrate to the aqueous layer and stirring it in a water bath, the silver nitrate will cloud up with AgCl after a few minutes. This is a commonly carried out reaction when learning basic organic chemistry at high school.
To solve the rate of reaction problem, try a phase transfer catalyst. I have been toying with the idea of benzalkonium chloride for this, basically it is a quarternary amine salt. The N being bonded to (in this case) a benzene ring and three alkyl groups (normally two methyl and one other, I believe), it will have a reasonable solubility in non-polar solvents due to all the alkyliness around. Thus the +ve ion is soluble in the non-polar layer to some degree, and as it dissolves it sort of drags whatever -ve ions are around in with it, in our case OH-, allowing them to react. That is probably a simplistic view of how they work, but it is how I think of it.
The benzalkonium chloride, although not tested (by me) is easily found in algaecides in garden centres, and would be cheap to try. There are a few things I want to try with it, but will have to wait until I get another condenser after mine was spectacularly ejected from a flask on a plume of NOx :D:(.
Other routes include ethylene epoxide and HCl, but then you'd have to make (and use) the epoxide, which is quite nasty, glycol and HCl (perhaps formed in situ with H2SO4 and NaCl), err, that's all I can think of.
I think whatever method you use, you will need some lab equipment to get a reasonably clean reaction.