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Author: Subject: Convert Your Alcohol to Acid
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[*] posted on 2-12-2006 at 00:00
Convert Your Alcohol to Acid


Here is an article using Nickel salt in bleach as a catalyst for efficiently oxidizing primary alcohols to their corresponding acids.

<b>Standard Procedure for the Oxidation of Primary Alcohols</b>
and Aldehydes. A 500 mL flask was charged with NiCl2 hexahydrate
(0.27 g, 1.14 mmol) and water (5 mL). A primary alcohol or
an aldehyde (45 mmol) was added followed by (optional) dichloromethane
(15 mL). The reaction was cooled in an ice bath, and
cold bleach (300 mL) was added in a steady stream over 5 min. A
fine black precipitate formed immediately. The resulting slurry was
stirred for 2 h at 0 °C and 2 h at room temperature. The slurry was
then acidified with 2 M hydrochloric acid until the aqueous layer
was strongly acidic by pH paper. The aqueous layer was extracted
with diethyl ether (3  100 mL). The combined organic extracts
were dried over anhydrous MgSO4 and filtered. Removal of the
solvent by rotary evaporation and brief high vacuum gave the crude
product. The purities could generally be improved to >98% by
distillation of the crude product or by recrystallization in the case
of solids.
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Attachment: Nickel-hypochlorite oxidizer.pdf (186kB)
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