Why thank you, Mountain Girl ^^
Here they are, people--a few refs to chew. Unfortunately, only a few, but enough to show it's possible.
Ning searched for HO.CH2CH(X).(ALH)2 --> HOOCCH(X).(ALH)2
The results are divided into three main types:
- K2Cr2O7 / H2SO4
- KMnO4 / NaOH
- HNO3
Most of the refs are for chromic acid, but since we here at the hive are environmentally conscious, I'll neglect those unless requested.
I. KMnO4 reactions
2-fluoroethanol --> fluoroacetic acid: Zh. Obshch.Khim 19, 111. Chem. Abstr. 1949, 6164 ; Kogyo Kagaku Zasshi 1955, 335. Chem. Abstr. 1956, 4063
several fluoroalcohols: Mol. Cryst. Liq. Cryst. 1991, 129
II. Nitric acid
Bull. Soc. Chim. Fr. 1876(!), 24
JACS 1950, 4353
USPT 2455405
Eur. J. Org. Chem. 2003, 526
III. Other
DMDO: Russ. Chem. Bl. 2000, 1332. Izv. Akad. Nauk Ser. Khim. 200, 1338.
They also used NaIO4/RuCl3, but I doubt y'all care about that.
Ning wonders whether KMnO4 under acidic conditions would work, or sodium persulfate + dilute sulfuric acid.
Hell, probably acidic bleach would work.
Polverone would be happy to know that HOEtF was one of the substrates oxidized.