Methyl-2-phenyl-propionate

Methyl Phenyl-propionate,—Phenyl-propionic acid, also known as hydrocinnamic acid, forms a methyl ester of the formula... 

Irganox 245 Ciba-Geigy, Switzerland Triethylenglycol-bis-3-(3-tert-butyl-4-hydroxy-5-methyl phenyl propionate)... 

Obtained by Fries rearrangement of 2-methoxy-6-methyl-phenyl propionate with aluminium chloride in refluxing carbon disulfide for 3 h (55%) [7390]. 

COCH2CH3 - Preparation by Fries rearrangement of 3-ethyl-jj 5-methyl-phenyl propionate (b.p.jg 142°) with... 

Preparation by Fries rearrangement of 2-tert-butyl-5-methyl-phenyl propionate with titanium tetrachloride in nitromethane at r.t. for 24 h (31%) [7025]. 

To a solution of (R/ ,SS)-2-methyl-3-phenyldimethylsilyl-3-phenyl-propionic acid (50 mmol) (see Chapter 8) in dichloromethane (50 ml),... 

C19H18N2O5 107754-15-4) see Zafirlukast methyl 3-(2-methoxy-5-methylphenyl)-3-phenyl-propionate... 

Phenyl-3-methyl-5-pyrazolone, 998 p-Phenylpl lenacy 1 bromide, 962 p-Phenylphenacyl esters, 363 Phenylpropiolic acid, 755, 776 Phenylpropionaldehyde, 906, 907 Phenyl propionate, 676... 

In the second method (Scheme 26) a 3-oxo ester is synthesized from an acid chloride and 2,2-dimethyl-l,3-dioxane-4,6-dione. Then, reductive amination of the 3-oxo ester with a-methyl(phenyl)methylamine provides a 3-amino- 3-alkyl propionic acid ester. This compound is then converted into the corresponding aldehyde, which is condensed with an eno-late to afford the final product. A representative synthetic procedure of this method is given in detail. 

If the filtrate is distilled under reduced pressure, 30 g of methyl 3-phenyl-propionate, b.p. 11 l-130°C/15mmHg, are obtained. When the distillation residue is dissolved in the minimum of hot ether and cooled, a further 1 g of the meso-adipate is obtained. The ether filtrate from this contains racemic dimethyl 3,4-diphenyladipate the latter may be recovered by evaporating the ether and crystallising the residue from the minimum of methanol m.p. 70-71 °C. 

Toguchi, H., Ogawa, Y., and Shimamoto, T. (1990) Effects of the physicochemical properties of the emulsion formulation on the bioavailability of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropyloxy)phenyl] propionate in ratsChem. Pharm. Bull., 38 2797-2800. 

A mixture of dl-2-[4-(2 -carboxymethyl-4 -methylphenoxy)phenyl]propionic acid (15.3 g) and polyphosphoric acid (92 g) was heated with stirring at 110-120°C for 2 hours. To the reaction mixture was added water and the resulting mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel (75 g) using chloroform as an eluent to give a crude product, which was recrystallized from toluene to give the dl-2-(8-methyl-10,ll-dihydro-ll-oxodibenz[b,f]oxepin-2-yl)propionic acid (9.4 g, 65.3%), m.p. 128-129°C. 

The oil described above was utilized directly in the condensation reaction with the epichlorohydrin. A mixture of 0.1 mole of methyl 3-(4-hydroxyphenyl)propionate, 0.2 mole potassium carbonate and 0.4 mole epichlorohydrin in 250 mL acetone was heated to reflux for 24 hours. The reaction medium was then filtered and evaporated. The residue was taken up in 100 mL toluene and washed with 100 mL 1.0 N NaOH and 100 mL water (2 times). The toluene phase was then dried over magnesium sulfate and evaporated to provide the crude product as an oil. Purification was effected by vacuum distillation (156°C/0.4 mm) and provided methyl 3-[4-(2,3-epoxypropoxy)phenyl]propionate. The NMR and IR spectra and elemental analysis data were consistent with the assigned structure. 

A solution of 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene (60.0 g) in methanol (500 ml) was hydrogenated at room temperature under one atmospheric pressure in the presence of 10% Pd-C (50% wet, 6.0 g). The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residual oil was dissolved in acetone (500 ml)-methanol (200 ml). To the solution was added a 47% HBr aqueous solution (152 g). The mixture was cooled, to which was added dropwise a solution of NaN02 (17.3 g) in water (30 ml) at a temperature not higher than 5°C. The whole mixture was stirred at 5°C for 20 min, then methyl acrylate (112 g) was added thereto and the temperature was raised to 38°C. Cuprous oxide (2.0 g) was added to the mixture in small portions with vigorous stirring. The reaction mixture was stirred until nitrogen gas evolution ceased, and was concentrated under reduced pressure. The concentrate was made alkaline with concentrated aqueous ammonia, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgS04) The solvent was evaporated off to leave methyl 2-bromo-3- 4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl propionate as a crude oil (74.09 g, 85.7%). 

A mixture of the crude oil of methyl 2-bromo-3- 4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl propionate (73.0 g) thiourea (14.2 g), sodium acetate (15.3 g) and ethanol (500 ml) was stirred for 3 hours under reflux. The reaction mixture was concentrated under reduced pressure, and the concentrate was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, to which were added water (200 ml) and ether (100 ml). The whole mixture was stirred for 10 min to yield 5- 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl -2-imino-4-thiazolidinone as crystals (0.3 g, 523.0%). Recrystallization from methanol gave colorless prisms, melting point 187°-188°C, dec. 

D-Phenyl propionates of methyl esters of racemic hydroxy acids were prepared by Hammarstrom and Hamberg [190] and used for the separation of enantiomers of these compounds on QF-1. The separation was successful with methyl 3-, 15-, 16- and-17-hydroxyoctadecanoates, whereas diastereoisomers of methyl 4-, 7- and 13-hydroxyocta-decanoic acids were not separated. The derivatives were prepared at room temperature reaction of the ester of the hydroxy acid with D-2-phenylpropionyl chloride in the presence of pyridine for 2 h. 

Dimethylamino-2,2-dimethyl-2//-azirine (23) and methyl 2-amino-3-phenyl-propionate gave 3-benzyl-5-dimethylamino-6,6-dimethyl-3,6-dihydro-2(17/)-... 

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