Post 326569 (https://www.thevespiary.org/talk/index.php?topic=9470.msg32656900#msg32656900)
(Chromic: "Calculations for THF =)", Methods Discourse), I took 5ml 10.8% bleach (5.7g, 8.3mmol, 1.9 eq) and added 0.35ml THF (0.32g, 4.4mmol, 1 eq). I wanted to use an excess of THF to judge the completion of the reaction on the disappearance of chlorine.Post 3958 (missing)
(Fuchem: "Oxidation of THF to GBL from Tetrahedron Letters", Chemistry Discourse))Does THF smell like acetone? What tests can I do to verify that what I have is actually THF?
No, THF and Acetone smell pretty different from each other. Don't quite know how to describe the THF smell, except maybe along the lines of a sickly Diethyl Ether-like scent. It REALLY stinks in SWIM's opinion.. If you get a big enough whiff (Not recommended, of course) you can taste the shit in the back of your throat, nasty indeed.
SpicyBrown
https://www.thevespiary.org/rhodium/Rhodium/pdf/thf2gbl.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/thf2gbl.pdf)
- not too common in journal articles nowadays, but in this case they were all there.Post 308130 (https://www.thevespiary.org/talk/index.php?topic=11867.msg30813000#msg30813000)
(moo: "THF oxidations", Novel Discourse) is exactly what I was looking for! Apparently 5 mol Br2 to 1 mol THF is the correct ratio.I'm completely convinced now, that [GBL] can't be made by aqueous oxidation using hypochlorite.
SWISM would like to report 32% yield after distillation, using aqueous Ca(OCl)2 & HCl, oxidizing THF to GBL, starting with 50g of THF (mostly-pure, distilled from pipe cement). He'd also like to report that this is one nasty reaction from an odour perspective, best to plan in advance where all the chlorine gas is going to go...
The crude GBL after recovering the extraction solvent (DCM) but before distillation was yellow, murky, and smelled somewhat chlorinated, lots of forerun during distillation, presumably chloro-hydrocarbons of some kind (or MEK, or both?)...
SWISM has just noticed a post on this reaction being done in DCM instead of H2O (but no acid?)... will most likely try that next!