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Topic: reduction of carboxylic acid to primary alcohol with LiAlH4  (Read 4671 times)

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Offline 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?

Offline discodermolide

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #1 on: June 29, 2011, 11:58:41 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
Development Chemists do it on Scale, Research Chemists just do it!
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Offline Smrt guy

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #2 on: July 03, 2011, 01:19:49 PM »
BH3 works or use an excess of LAH

Offline discodermolide

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #3 on: July 03, 2011, 02:16:20 PM »
BH3 works or use an excess of LAH
Work up is easier with BH3
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Offline orgopete

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Re: reduction of carboxylic acid to primary alcohol with LiAlH4
« Reply #4 on: July 04, 2011, 02:33:16 PM »
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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