Just a quick question, out of general interest really, has anyone ever seen THF react with HCl to form 4-chlorobutanol?
I am doing a reaction with sodium nitrite and Conc. HClaq in THF at 20°C and the GCMS of the reaction mixture shows a small but significant peak which gives a NIST search of 4-chlorobutanol. I have no doubts about it as the MS matches and the isotope ratio of the molecular ion is as predicted.
I have never seen this before with THF so I was wondering whether it was due to the presence of nitrous acid or if anyone else had seen this type of ring opening with strong aqueous acid.