Catalytic Transesterification Routes to Novel Vinyl Glycolate Derivatives of Polyhydric Alcohols

Abstract

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New bifunctional monomers from methyl vinyl glycolate

“…Reported reactions of MVG include its dimerization to maple furanone, thiol-ene reaction, cyclization to a lactide-like dimer, Claisen rearrangement, homo and cross metathesis of the CQC group, allylic rearrangement and transesterification. 16,17 a-Hydroxy acids such as lactic and glycolic acid are of interest for their application in the production of biocompatible, biodegradable and renewable polyesters. [18][19][20][21] MVG, being itself an a-hydroxy acid ester, has been incorporated as a co-monomer into poly(L-lactic acid) (PLLA).…”

“…By this approach we envisage that hydroformylation could be effectively applied to upgrade MVG to novel useful monomers for polymers, for example as diester or diacid, hydroxyester, diols or triols that can have several applications, for example as monomers and crosslinker for polyesters. 17 The methoxycarbonylation of MVG was attempted by applying the well-established combination of palladium(II) acetate, a,a 0 -bis(di-t-butylphosphino)-o-xylene (Lucite Alpha ligand, dppx) and methylsulfonic acid. 28,29 However, the desired product (Scheme 2a, 4) could not be detected: reduction of the double bond took place, affording the saturated methyl 2hydroxy-butyrate (5) which was isolated in quantitative yield.…”

“…By this approach we envisage that hydroformylation could be effectively applied to upgrade MVG to novel useful monomers for polymers, for example as diester or diacid, hydroxyester, diols or triols that can have several applications, for example as monomers and crosslinker for polyesters. 17…”