Phenyl-glycidic acid

Methyl-3-phenyl glycidic acid ethyl ester... 

This knowledge was applied for even more complicated, bifunctional compounds such as phenyl glycidic acid methyl ester 3 to yield alpha-ketone carboxylic acid esters 4 such as 3-phenylpyroracemic acid methylesters (Eq. 15.2.2). 

Fig. 15.2 Catalyst screening for the conversion of phenyl glycidic acid methyl ester to 3-phenylpyroracemic acid methylester...

By increasing the temperature over > 300°C, the phenyl glycidic acid esters are converted to phenyl acid esters. That occurs in a consecutive decarbonylation of a-ketone carboxylic acid esters as intermediate. In the case of p-tert-butyl glycidic acid ester in the presence of a boron-pentasil zeolite at 350 °C the ratio between a-ketone carboxylic acid ester and the phenyl acetic acid ester is 65 35. 

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

One part aZp/ia-methyl-B-(phenyl)-glycidic acid is mixed with 2 parts of copper chromite and heated at a temperature of 130-140° C. under reduced pressure for 2 hours. The oily product is distilled. The distillate collected is phenyl acetone. 

Phenyl-glycidic Acid Chapter 20 Preparation of Phenyl-glycidic Acids... 

If the phenyl glycidic acid esters contain t-butyl- or i-propyl groups on the ester residue decarbonylation and elimination of an olefin occurs in the presence of acidic heterogeneous catalysts at temperatures > 200 °C to form phenylacetalde-hydes with high selectivity (> 80% at 100% conversion) [8]. 

An example of an industrial membrane bioreactor is the hollow-fiber membrane system for the production of (-)-MPGM (1), which is an important intermediate for the production of diltiazem hydrochloride [130, 131]. For the enantiospecific hydrolysis of MPGM a hoUow-fiber ultrafiltration membrane with immobilized lipase from Serratia marcescens is used. (-i-)-MPGM is selectively converted into (2S,3R)-(-i-)-3-(4-methoxy-phenyl)glycidic 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. 5.17). Enantiomerically pure (-)-MPGM is obtained from the toluene phase by a crystallization step. In cooperation with Sepracor Inc., a pilot-plant membrane reactor has been developed, which produces annually about 40 kg (-)-MPGM per m of membrane surface. 

Yamaguchi T, Harada N, Ozaki K, Hayashi M, Arakawa H, Hashiyama T (1999) Synthesis of Taxoids 4. Novel and Versatile Methods for Preparation of New Taxoids by Employing cis- or trans-Phenyl Glycidic Acid. Tetrahedron 55 1005... 

Ethyl 2,3-epoxy-3-methyl-3-phenylpropionate Ethyl 3-methyl-3-phenylglycidate Ethyl 3-methyl-3-phenyloxiranecarboxylate 3-Methyl-3-phenyl glycidic acid ethyl ester 3-Methyl-3-phenyloxiranecarboxylic acid, ethyl ester Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester Strawberry aldehyde Ciassification Organic compd. 

Methyl phenylethyl ketone Methyl 2-phenylethyl ketone. See Benzylacetone 3-Methyl-3-phenyl glycidic acid ethyl ester. See Ethyl methylphenylglycidate Methylphenylglyoxal. See 1-Phenyl-1,2-propanedione Methyl phenylglyoxalate CAS 15206-55-0 EINECS/ELINCS 239-263-3 Synonyms Benzeneacetic acid, a-oxo-, methyl ester Methylbenzoylformate Methyl a-ketophenylacetate Methylphenylglyoxylate Oxo-phenylacetic acid methyl ester Classification Aromatic ester Empirical CgHaOs... 

PHENYLMETHYLGLYCIDIC ESTER (Glycidic acid, (3-methyl-(J-phenyl-, ethyl ester)... 

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. 

GlyCIDIC acid, 3-METHYL-3-PHENYL-ETHYL ESTER, 24, 82... 

The mechanism of gas-phase decomposition of ethyl and ethyl 3-phenyl glycidate has been studied by DFT and MP2 methods. The results indicated that the ethyl group is eliminated as ethylene through a concerted six-membered cyclic TS, and the unstable intermediate glycidic acid decarboxylates rapidly to give the corresponding aldehyde via a five-membered cyclic TS. 

Oxiranes such as benzyl glycidate and glycidiyl phenyl ether were polymerized with succinic anhydride in the presence of PPL at 60 or 80°C (137,138). The reaction of succinic anhydride with serine residue of the lipase catalyst produces a carboxylic acid moiety, which might act as acid catalyst for ring-opening of oxirane. 

---