Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1997-03-10
1999-02-16
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560129, 568877, C07C 6702
Patent
active
058722777
ABSTRACT:
Methods for preparing 3-methyl-2-buten-1-ol (prenyl alcohol) from 2-methyl-1,3-butadiene (isoprene) and carboxylic acids are disclosed. Carboxylic acids which can be used in the process have a K.sub.a (relative to water) greater than 10.sup.-4 ; dichloroacetic acid is especially preferred. The process involves the slow (e.g., dropwise) addition of isoprene to the carboxylic acid to form a prenyl ester. The ester-formation reaction proceeds at room temperature in most cases; use of an organic base catalyst, preferably a sodium or potassium salt of the reactant carboxylic acid, improves the yield. The resultant prenyl ester can be converted to prenyl alcohol by reaction with a base. Prenyl alcohol can be readily converted to citral, a chemical intermediate in the synthesis of vitamins A and E, and several widely-used carotenoids.
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Killos Paul J.
Loyola University of Chicago
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