How to convert ethanol to 1,1-dichloroethane?

How to convert ethanol to 1,1-dichloroethane?


My approach: Convert ethanol to ethene followed by $\ce{HCl}$ addition. But that's no use. Well if it is possible to create gem-diol from here, then maybe it can be done. But not getting a suitable reaction. Can't seem to figure out anything. Please help!





> 
> convert ethanol to 1,1-dichloroethane?
> 
> 
> 


A standard route for producing gem-dichloro compounds involves treatment of a ketone or aldehyde with $\ce{PCl5}$ (see the second to last paragraph in the "Chlorination of organic compounds" section [here](https://en.wikipedia.org/wiki/Phosphorus_pentachloride) and page 18 [here](https://books.google.com/books?id=0RQEsfYCuBcC&pg=PA2&lpg=PA2&dq=synthesis%20of%20gem-dichloro%20compounds&source=bl&ots=RZqIIMocxM&sig=SLtiMoFXiJn48r3RdQopDJV2d8I&hl=en&sa=X&ved=0CCUQ6AEwAWoVChMI3Obav8HYxwIVS8uACh35lAMS#v=onepage&q=synthesis%20of%20gem-dichloro%20compounds&f=false)).


[![enter image description here](https://i.stack.imgur.com/hGuD0.png)](https://i.stack.imgur.com/hGuD0.png)


([image source](https://en.wikipedia.org/wiki/Geminal))


Therefore, you could carefully oxidize your ethanol to acetaldehyde and treat it with $\ce{PCl5}$.


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