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Author Topic: reduction of carboxylic acid to primary alcohol with LiAlH4  (Read 2609 times)

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xaxax

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I want to carry out the reaction of primary alcohol from carboxylic acids. I will add carboxylic acid and LiAlH4 into the flask in dry diethyl ether, and i will do this reaction at 30C for 2 hours.
while there is produced alcohol, there is also produced water, and water reacts with LiAlH4 quickly.
how should i do this reaction?
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discodermolide

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #1 on: June 29, 2011, 05:58:41 PM »

I want to carry out the reaction of primary alcohol from carboxylic acids. I will add carboxylic acid and LiAlH4 into the flask in dry diethyl ether, and i will do this reaction at 30C for 2 hours.
while there is produced alcohol, there is also produced water, and water reacts with LiAlH4 quickly.
how should i do this reaction?

Use BH3.DMS
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Smrt guy

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #2 on: July 03, 2011, 07:19:49 AM »

BH3 works or use an excess of LAH
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discodermolide

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #3 on: July 03, 2011, 08:16:20 AM »

BH3 works or use an excess of LAH
Work up is easier with BH3
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orgopete

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #4 on: July 04, 2011, 08:33:16 AM »

If you start with an acid, a borate ester intermediate will react better than the lithium salt of your acid. I too prefer doing a diborane reduction.
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