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Browse Prior Art Database

Synthesis of Omega Hydroxy Esters

IP.com Disclosure Number: IPCOM000096248D
Original Publication Date: 1963-Mar-01
Included in the Prior Art Database: 2005-Mar-07
Document File: 1 page(s) / 12K

Publishing Venue

IBM

Related People

McGee, HL: AUTHOR

Abstract

Priorly, the synthesis of omega hydroxy esters involved ozonolysis of the ester of unsaturated fatty acid and the consequent reduction of the Ozonide to get the hydroxy ester. The main drawback of this synthesis is the limitation as to chain length that is placed on the omega hydroxy, acid. Since the point of unsaturation is generally at the ninth or tenth carbon atom, the chain length of the Omega hydroxy acid is limited to ten carbon atoms. This synthesis involves the reduction of the acyl chloride of the half ester of a dicarboxylic acid with sodium borohydride. In this, advantage is taken of the reactivities of the acyl chloride and ester moieties. The ester grouping is slowly attacked by the reductant while there is a great reactivity with the acyl chloride portion. The resultant reduction gives the omega hydroxy ester.

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Synthesis of Omega Hydroxy Esters

Priorly, the synthesis of omega hydroxy esters involved ozonolysis of the ester of unsaturated fatty acid and the consequent reduction of the Ozonide to get the hydroxy ester. The main drawback of this synthesis is the limitation as to chain length that is placed on the omega hydroxy, acid. Since the point of unsaturation is generally at the ninth or tenth carbon atom, the chain length of the Omega hydroxy acid is limited to ten carbon atoms. This synthesis involves the reduction of the acyl chloride of the half ester of a dicarboxylic acid with sodium borohydride. In this, advantage is taken of the reactivities of the acyl chloride and ester moieties. The ester grouping is slowly attacked by the reductant while there is a great reactivity with the acyl chloride portion. The resultant reduction gives the omega hydroxy ester. Long chain omega hydroxy esters can be obtained by forming half esters of longer dicarboxylic acids. The following illustrates a typical synthesis: Ethyl 10 hydroxy decanoate

To a flask is added 49 g (. 2 mole) of ethyl sebscyl chloride, 500 ml of redistilled dioxane and 15. 1 g (. 4 moles) of sodium borohydride. The mixture is stirred and allowed to react for 16 hours at room temperature. The reaction is then stopped by adding the mixture to 500 g of crushed ice containing 10 ml of concentrated hydrochloric acid. This results in a vigorous reaction with the evolution of hydrogen.

The aqueous phase is then ex...