Ethyl 3-phenyl- 3-hydroxypropionate

Ethyl /3-phenyl-/3-hydroxypropionate has been prepared by esterification of /3-phenyl-/3-hydroxypropionic acid obtained by the addition of hydrogen bromide to cinnamic acid and subsequent hydrolysis.1,2 The procedure given is based on that of Andrijewski 3 and of Blaise and Herman.4... 

Ethyl a-bromoisobutyrate, 21, 53 Ethyl /3-bromopropionate, 20, 6S Ethyl caprylate, 20, 69 Ethyl carbonate, 23, 95, 97 Ethyl chlorocarbonate, 21, 81 2-Ethylchromone, 21, 42 Ethyl diacetylacetate, 21, 46 copper derivative, 21, 46 Ethyl a,a-DIMETHYL-/3-PHENYL-/3-hydroxypropionate, 21, S3 Ethylene chloride, 20, 28 22, 76 ETHYLENEDIAMINE, IV IV-DIBUTYL-, 23, 23... 

Ethyl a,a-dimethyl-/3-phenyl- 3-hydroxypropionate may be prepared in a similar manner. For instance, from 100 g. of ethyl a-bromoisobutyrate and 65 g. of benzaldehyde, 82.5 g. (73 per cent of the theoretical amount) of ethyl a,a-dimethyl-/3-phenyl-/3-hydroxypropionate, boiling at i53-i58°/n mm., is obtained. It may be recrystallized by dissolving it at 30° in 100 cc. of ligroin (30-60°), chilling the solution for several days, and decanting the clear liquid from the precipitate m.p. 38.5-39°. 

Benzaldehyde dimethylacetal (200 pi, 1.33 mmol) and a catalytic amount of p-toluenesulfonic acid (37 mg) are added to methyl (2R,3S)-3-(4-nitrobenzenesulfonamido)-3-phenyl-2-hydroxypropionate (315 mg, 0.83 mmol) in toluene 5 ml. The mixture is heated at 100°C under reduced pressure (15 mm mercury) with no condenser. After 1 h the crude reaction mixture is diluted with ethyl acetate and washed with water (2 times). After drying the organic layer over magnesium sulfate the crude material is purified by column chormatography (silica gel eluting with ethyl acetate/cyclohexane, 35/65) to give the (2S,4S,5R)-2,4-diphenyl-3-(4-nitrobenzenesulfonamido)-5-methoxycarbonyl-l,3-oxazolidine, melting point 118°-120°C. 

Finanz New Method of Synthesis of Ethyl Esters and Methyl Amides of 3-Phenyl-3-(4-Pyridyl)-3-Hydroxypropionic Acid and 3-Phenyl-3-(2-Pyridyl)-3-Hydroxypropionic Acid 1968 GB 1,106,517... 

Within the framework of studies of the mechanism of fragmentation of 2-phenyl-oxetane by electron bombardment in the ion source of a mass spectrometer 2-phenyloxetanes labelled with stable isotopes were needed104. 2-Phenyloxetanes, 157, labelled with fH (and 13C) in different positions have been synthesized according to four-step reaction schemes shown in equations 68 and 69105. In the first step, isotopically (D- or 13C) labelled benzaldehyde has been coupled with ethyl bromoacetate in the presence of Zn and dimethoxymethane. The deuterated 3-phenyl-3-hydroxypropionate obtained has been reduced with lithium aluminium hydride. In the next step the primary alcohol group of the deuterated phenyl propanediol 158 has been tosylated. Cyclization of the monotosylates 159 yielded 13C- or deuterium-labelled 2-phenyloxe-oxtanes 157. 

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