Lactic acid, allyl ester

ALLYL LACTATE (Lactic acid, allyl ester)... 

A benzyl carbonate was prepared in 83% yield from the sodium alkoxide of glycerol and benzyl chloroformate (20°, 24 h). It was also prepared by a lipase-catalyzed ester exchange with allyl benzyl carbonate. It is cleaved by hydrogenolysis (H2/Pd-C, EtOH, 20°, 2 h, 2 atm, 76% yield) and electrolytic reduction (—2.7 V, R4N X, DMF, 70% yield). A benzyl carbonate was used to protect the hydroxyl group in lactic acid during a peptide synthesis." ... 

Esterification—Continued by azeotropic distillation with benzene, 22, 38 by nitric acid, 22, 65 of desoxycholic acid, 24, 41 of lactic acid, 26, 4 of linoleic acid, 22, 77 of linolenic acid, 22, 83 of pyruvic acid with use of methyl ester column, 24, 72 Ester interchange, 26, 5, 19 between polylactic acid and allyl alcohol, 26, 5... 

In contrast to the extensive use of glycolate esters, lactate, mandelate and other higher a-oxygenated esters have been used much less frequently. Early work by Bartlett et al. showed that the Ireland-Claisen rearrangement could be used to prepare allylated lactic acids in good yield, but the diastereoselectivity was disappointingly low (Scheme 4.75) [20]. 

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