Alcohols, primary with chromyl chloride

Oxidation, of primary alcohols to aldehydes, 52, 5 of terminal olefins with chromyl chloride, 51, 6 of 2,4,4-trimethyl-1-pentene with chromyl chloride, 51, 4 with chromium trioxide-pyridine complex, 52, 5... 

It reacts with olefins forming their chromyl chloride derivatives which on hydrolysis yield chloroalcohols (chlorohydrins) that are mostly the B-chloro-primary alcohols ... 

The reaction of chromyl chloride with alkenes gives epoxides, chlo-rohydrins, chloroketones, and ketones [668, 667, 668, 669, 670] or aldehydes (in the presence of zinc) [671, 672]. Benzene homologues are oxidized to aldehydes [667, 668] or ketones [666, 668, 673], Primary alcohols are converted into aldehydes [674, 675], and trimethylsilyl ethers of enols are transformed into a-hydroxy ketones [676]. 

Several references have appeared on the use of solid-phase oxidants. Solid potassium permanganate-copper sulphate mixtures oxidize secondary alcohols to ketones in high yield, and pyridinium chromate or chromic acid on silica gel are described as convenient off-the-shelf reagents for oxidation of both primary and secondary alcohols. Anhydrous chromium trioxide-celite effects similar transformations only when ether is present as co-solvent. An excellent review, with over 400 references, on supported oxidants covers the use of silver carbonate-celite, chromium trioxide-pyridine-celite, ozone-silica, chromyl chloride-silica, chromium trioxide-graphite, manganese dioxide-carbon, and potassium permanganate-molecular sieve. 

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