From glycidic acids

Boron fluoride y6, y-Ethylene-a-hydroxycarboxylic from glycidic acid esters s. 32,127 BF, ->C C-C(OH)... 

Lead tetraacetate/sodium salt a-Acetoxyaldehydes from glycidic acids... 

Aminohydroxycarboxylic acid amides from glycidic acid esters s. 13, 360... 

A number of 5-hydroxy-2-oxotetrahydro-l,3-oxazine derivatives can also be formed from glycide esters of carbamic acid ... 

An example of an industrial membrane bioreactor is the hollow-fiber membrane system for the production of (-)-MPGM (3-(4-methoxyphenyl)glycidic acid methyl ester), which is an important intermediate for the production of diltiazem hydrochloride [81, 82]. For the enantiospecific hydrolysis of MPGM a hollow-fiber ultrafiltration membrane with immobilized lipase from Serratia marcescens is used. (-f)-MPGM is selectively converted into (2S,3J )-(-F)-3-(4-methoxyphenyl)glyci-dic acid and methanol. The reactant is dissolved in toluene, whereas the hydrophilic product is removed via the aqueous phase at the permeate side of the membrane, see Fig. 13.9. EnantiomericaUy pure (-)-MPGM is obtained from the to-... 

Epoxides (see also a,(3-Epoxy alcohols, etc., Glycidic acids, esters, nitriles) From alkenes by epoxidation Dimethyldioxirane, 120 Fluorine-Acetonitrile, 135 Potassium peroxomonosulfate, 259 From carbonyl compounds Alumina, 14... 

Aromatic and aliphatic aldehydes have been prepared in good yields by the decarboxylation and isomerization of the corresponding glycidic acids. Esters of the latter are obtained by treating a ketone with ethyl chloro-acetate in the presence of sodium amide (method 127). The glycidic esters are first converted to the sodium salts with sodium ethoxide and then treated with aqueous hydrochloric acid under gentle reflux. By this procedure, a-phenylpropionaldehyde has been prepared from acetophenone in an over-all yield of 38%. Other details have been discussed. ... 

Glycide alcohol or glycidol, which is 1,2-anhydro glycerol, is not available as a precursor of glycogen in the white rat and it cannot serve as a substrate from which acid and gas can be formed by various microorganisms. ... 

When the glycidic acid ester is to be further worked up to the phenylacetaldehyde it need not previously be distilled, but the crude ester is saponified with sodium hydroxide while steam is passed through it, and an organic acid, for instance oxalic acid, and sulphuric acid are added. Carbon dioxide is eliminated from the glycidic acid thus liberated and the phenyl-acetaldehyde distills with water. 

Preparation of Phenyl-2-propanone from a/p/ia-Methyl-B-(phenyl)-glycidic Acid... 

An immobilized lipase, from M. miehei, was used by Aaltonen s group for the kinetic resolution of tra w-3-(4-methoxyphenyl)glycidic acid methyl ester [Eq. (13)], a precursor in the preparation of the calcium antagonist drug diltiazem (91) ... 

The lipase from Serratia marcescens has a high enantioselectivity (E = 135) for the (2R,3S)-(4-methoxyphenyl) glycidic acid methyl ester, which acts as a competitive inhibitor. The formed acid (hydrolyzed (+)-methoxyphenylglycidate) is unstable and decarboxylates to give 4-methoxyphenylacetaldehyde this aldehyde strongly inhibits and deactivates the enzyme. It is removed by transfer to the aqueous phase by formation of a water-soluble adduct with sodium hydrogen sulfite added to the aqueous phase. The bisulfite acts also as a buffer to maintain constant pH during synthesis. 

Kinetic Resolution of Glycidic Acid Methyl Ester by Lipase from Serratia marcescens (E.C. 3.1.1.3) 1430... 

Pyridazines have been prepared from a variety of other heterocyclic systems and in most cases these transformations were specific. The 3(S), 4(5) 36, a constituent of the antibiotic antitumor luzopeptin A, was prepared in a multistep synthesis from malonaldehyde dimethyl acetal in 32% overall yield. In the last step a highly regiospecific nucleophilic ring opening of the glycidic acid (oxirane derivative) took place (89JOC3260). In another example, c75,frani-l,3-cycloundecadiene was transformed in five steps in low yield into 59. In the last step the epoxide 58 was treated with excess of LDA (89TL4649). 

By analogy with the rearrangement of styrene oxide compounds, more complicated substances, e. g. phenylpyruvic acid methyl ester derivatives, can be synthesized from readily available glycidic acid esters, as shown in Figure 3. These esters can be used as intermediates for herbicides (e. g. the triazinones) and for the synthesis of L-amino acids. 

Darzens-Claisen reaction Glycidic acid esters from a-halogenocarboxylic acid esters and oxo coumpounds... 

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