[Annna]

HI!

I was refluxing a solution of carboxylic acid and thionyl chloride to get an acid chloride, when suddenly the temp. suddenly dropped and the solution became full of water

Is there anyway i can get my carboxylic acid or acid chloride back?

The solution precipitated when water was added, so maybe some kind of salt has been formed, or maybe my its my carboxylic acid (solid).. I am thinking about vaporising the filtrate and get rid of the water and thionyl chloride, to get my acid chloride (liquid)..

[discodermolide]

Your acid chloride has probably been hydrolysed back to the acid.
The best way to recover the acid is probably to make the solution basic (NaOH) this will form the acid salt, water soluble. Wash this with a solvent, just to ensure any non-acidic organic material is removed. Then re-acidify the aqueous layer with hydrochloric acid. Now here your acid may precipitate, that's fine, filter and dry the solid. If not then extract into organic, remove organic and you have your acid back.

[Annna]

Okay, so I'm gonna add NaOH to my solution, and the carboxylic acid salt will form.

Should I then add a solvent to the solution and then extract unwanted organic material, or how should I wash it? What could that solvent for example be? Ether?

Afterwards I'm gonna add hydrochloric acid (and i guess NaCl will form and i will get my acid back) and then dry if it precipitates or otherwise extract. Should I use ether for the extraction?

[opsomath]

Wait, I don't understand. When you say "it became full of water" what exactly happened? You mean you popped a hose and liquid water actually spilled in?

[discodermolide]

Okay, so I'm gonna add NaOH to my solution, and the carboxylic acid salt will form.

Should I then add a solvent to the solution and then extract unwanted organic material, or how should I wash it? What could that solvent for example be? Ether?
Afterwards I'm gonna add hydrochloric acid (and i guess NaCl will form and i will get my acid back) and then dry if it precipitates or otherwise extract. Should I use ether for the extraction?

You could use ether for both extractions. But for the second one the acid may not be ether soluble so use something a bit more polar.
Use your imagination as to which solvents to use, you know your compound, I don't

[Annna]

Discodermolide: Thank you so much! I'm gonna try it 


Opsomath: Sorry, it's because english is not my mother tongue 

I had made a gas trap (used and empty flask, and then a flask with water), because of the HCl gas and the temp. dropped for some reason and water was sucked into the system.. I had turned the empty flask the wrong way, if that makes sense