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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: xaxax on June 29, 2011, 12:57:47 PM

Title: reduction of carboxylic acid to primary alcohol with LiAlH4
Post by: xaxax on June 29, 2011, 12:57:47 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?
Title: Re: reduction of carboxylic acid to primary alcohol with LiAlH4
Post by: discodermolide 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
Title: Re: reduction of carboxylic acid to primary alcohol with LiAlH4
Post by: Smrt guy on July 03, 2011, 07:19:49 AM
BH3 works or use an excess of LAH
Title: Re: reduction of carboxylic acid to primary alcohol with LiAlH4
Post by: discodermolide on July 03, 2011, 08:16:20 AM
BH3 works or use an excess of LAH
Work up is easier with BH3
Title: Re: reduction of carboxylic acid to primary alcohol with LiAlH4
Post by: orgopete 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.