Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Computed Properties of C11H14O3
The synthesis of mandelic acid analogs. II. Styrylglycolic acids was written by Nerdel, Friedrich;Rachel, Hans. And the article was included in Chemische Berichte in 1956.Computed Properties of C11H14O3 This article mentions the following:
Adding dropwise 54 cc. concentrated HCl to 80 cc. PhCH:CHCHO and 49 g. NaCN in 250 cc. Et2O cooled with ice, stirring the mixture 1 hr. at 0° and 1 hr. at 20°, washing the filtered Et2O solution with concentrated NaHSO3 and recrystallizing the residue from CS2 give 65-70% DL-PhCH:CHCH(OH)CN (I), m. 74-5°. Adding dropwise at below 10° a mixture of 250 cc. concentrated HCl and 40 cc. concentrated H2SO4 to 90 g. I in 200 cc. Et2O, warming the mixture 0.5 hr. at 15°, and diluting it after several hrs. with 3-4 fold ice-H2O give up to 85% DL-styrylglycolic acid (II) amide, m. 141°, which (10 g.), refluxed 1 hr. with 15 g. (CO2H)2 in 200 cc. H2O, gives 80% II, m. 137°. Concentrating slowly in vacuo a mixture of 30 g. (+)-bornylamine (III) in 200 cc. Et2O and 30 g. II in 200 cc. MeOH until 2/3 of the solvents are evaporated, filtering off the precipitate; [α]D 18°, and recrystallizing it 7-8 times from Me2CHOH give 20 g. III D-styrylglycolate, [α]D 28° (MeOH). Recrystallizing the residue of the original mother liquor several times from H2O gives 10 g. III L-styrylglycolate, [α]D -6°. Decomposition of the salts gives D-II, m. 139° (decomposition), [α]D 100° (MeOH), and L-II (-)-isomer, m. 139°, [α]D -98°. Hydrogenation of D-II in MeOH 5 min. with PtO2 gives 100% (+)-α-hydroxy-γ-phenylbutyric acid (IV), m. 114-15°, [α]D20 10.4° (EtOH). Refluxing 4.5 g. IV in 135 cc. absolute MeOH 16 hrs. with 5 cc. concentrated H2SO4 gives 4 g. Me ester (V), b16 155-7°, [α]D20 23° (C6H6). Shaking 3 g. V 6 hrs. with 50 cc. supersaturated NH3-NH4OH gives the amide (VI), needles, m. 124°, [α]D20 -37° (MeOH); DL-amide, m. 130°. Bromination of D-II in CHCl3 gives (-)-α-hydroxy-β,γ-dibromo-γ-phenylbutyric acid (VII), m. 177° (decomposition), [α]D20 -60° (MeOH). Condensation of 36 g. m-O2NC6H4CH:CHCHO in 300 cc. CHCl3 with 42 g. NaCN and 22 cc. 35.4% HCl as above gives 70-80% (3-nitrostyryl)glycolic acid (VIII) nitrile (IX), m. 76-8°, which, treated with BzCl and C5H5N, gives the O-Bz derivative, m. 111°. Treating 32 g. IX in 200 cc. Et2O with 79 cc. concentrated HCl and 12.6 cc. concentrated H2SO4 3 days at 20°, pouring the mixture into ice-H2O, extracting with Et2O, and recrystallizing the residue of the Et2O extract give 20-22 g. VIII, slightly yellow needles, m. 130-5° (decomposition), which, treated with Br in CHCl3, gives α-hydroxy-β,γ-dibromo-γ-(3-nitrophenyl)butyric acid, m. 175-6° (decomposition). Resolution of VIII with III gives a III (+)-VIII salt, [α]D20 24° (MeOH), from which the free (+)-VIII, m. 112-17°, [α]D20 71°, is obtained on decomposition with HCl. Hydrogenation of (+)-VIII in MeOH with PtO2 gives (+)-α-hydroxy-γ-(3-aminophenyl)butyric acid (not quite pure), [α]D20 0.75° (MeOH), which, diazotized and treated with Cu2H2, gives (+)-α-hydroxy-γ-phenylbutyric acid, m. 113°, [α]D20 10.6°. Hydrogenation of 20 g. β-phenylglycidic acid Et ester in 50 cc. EtOH with 2 g. Raney Ni 8 hrs. at 20° and atm. pressure gives PhCH2CH(OH)CO2Et, b16 153°, which, saponified with NaOEt, gives the free acid, m. 96° (Ac derivative, m. 72°; amide, m. 112°). The equilibrium constants of the m- and p-substituted PhCOMe are determined to be, resp.: NO2, 0.43, 0.28; Br, 0.77, 1.2; MeO, 1.27, 7.4; NHAc, 1.31, 6; Me, 1.53, 3; OH, 1.47, 14; H, 1.52, 1.52; NH2, 1.73, 18; PhCH:CHCHO, 0.032; 3-NO2 analog, 0.023; 3-O2NC6H4COMe, 0.43. The rotation dispersions of D-II, VI, VII, and VIII in MeOH, EtOH, dioxane, Me2CO, AcOH, and NaOH are given in tables. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0Computed Properties of C11H14O3).
Ethyl 2-hydroxy-3-phenylpropanoate (cas: 15399-05-0) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Computed Properties of C11H14O3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics