16 Phenyl propionate

The ester and catalj st are usually employed in equimoleciilar amounts. With R =CjHs (phenyl propionate), the products are o- and p-propiophenol with R = CH3 (phenyl acetate), o- and p-hydroxyacetophenone are formed. The nature of the product is influenced by the structure of the ester, by the temperature, the solvent and the amount of aluminium chloride used generally, low reaction temperatures favour the formation of p-hydroxy ketones. It is usually possible to separate the two hydroxy ketones by fractional distillation under diminished pressure through an efficient fractionating column or by steam distillation the ortho compounds, being chelated, are more volatile in steam It may be mentioned that Clemmensen reduction (compare Section IV,6) of the hj droxy ketones affords an excellent route to the substituted phenols. 

The phenyl propionate may be prepared by slowly adding 196 g. (120 ml.) of redistilled thionyl chloride to a mixture of I50g. of pure phenol and 132 g. (133 ml.) of propionic acid (compare Fig. 111,31, 1), warming to drive all the sulphur dioxide and hydrogen chloride, and distilling 190 g. of phenyl propionate, b.p. 202-212° (the pure substance boils at 211°) are obtained. 

Triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxy-phenyl)propionate] [36443-68-2]... 

Benzoyl-2,3-dihydro-lH-pyrrolizine-l-cai boxylic acid (ketorolac, L ) and 2-(3-benzoyl-phenyl)propionic acid (ketoprofen, L ) ai e biologically activ ligands used in medicine as non-steroidal anti-inflammatory dmgs. 

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

Phenyl-propionitrile, CgHj. CH.2. CH2. CN, is present in nssturtium oil. It is a powerfully smelling oil, boiling at 261°. On hydrolysis by alcoholic potash it yields phenyl-propionic acid, melting at 47°. 

The mixture of 7.9 g of ethyl a-(4-aminophenyl)propionate and 8.3 g of ethyl 2-chloro-methylbenzoate is refluxed under nitrogen for one hour. The residue is recrystallized from hexane, to yield the ethyl a-[4-(1-oxo-isoindolino)-phenyl]-propionate of the formula... 

The pure dimethylaminoethanol salt was dissolved in 400 ml of 50% acetic acid at 90°C and then cooled to 5°C. The solid which precipitated was collected by filtration, washed with water, cold 50% acetic acid and finally with low-boiling petroleum ether. After drying in vacuo there was obtained 24 g of hydrated dextro-/3-(3,5-diiodo-4-hydroxy)-a-phenyl-propionic acid, MP 80° to 85°C. 

C. Hydrolysis of Ethyl a, fi-Dicyano- -phenyl Propionate — The product thus obtained is hydrolyzed by boiling under a reflux condenser for four hours with 80 cc. of concentrated hydrochloric acid (sp. gr. 1.19). The substance goes into solution and this clear solution, on cooling, deposits phenylsuccinic acid in small crystals which are nearly colorless. These are filtered off, washed with cold water and dried. The yield of product melting at 164-166° is 17.6-18.4 g. (91-95 per cent of the theoretical amount based on the weight of ester used) (Notes 1 and 2). 

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

Polyphosphoric acid in cyclization of ethyl a-acetyl-/3-(2,3-dimethoxy-phenyl)propionate to 6,7-dimeth-oxy-3-methylindene-2-carboxyl-ate, 40, 43... 

C25H27CIO3 /O/Oy-i -J) see Trenbolone acetate ( )-2-chioro-3-[4-[(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)incthoxy]phenyl]propionic acid (C23H27C10 97322-69-5) sec Troglitazone 4 -chloro-2 (24midazoUn-2-yl)benzophenone (Ci HjiClNjO 22590-J7-6) see Mazindo ... 

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

NMR-spectroscopic studies and a single crystal X-ray structure determination of the reduced Co / form of 100 revealed the presence of a bridging 2,3-dibromo-3-phenyl-propionato ligand (threo dl pair). The complex bearing the erythro form of 2,3-dibromo-3-phenyl-propionate is only produced in minor yields <3%. Therefore, the bromination of the encapsulated alkene is a highly diastereoselective syu-addition. This is rather... 

Methyloxindole has been prepared by the reduction of a-(2-nitro-phenyl)propionic acid,2 by heating j8-propionylphenylhydrazine with lime3 or with sodium alkoxides,4 and by reduction of the benzoyl derivative of oxindole-3-aldehyde.6... 

Ethyl a-ACETYL-/3-(2,3-DiMETHOXY-phenyl)propionate, 31, 56 Ethyl a-acetyl-/3-(3,4-dimethoxyphenyl)-propionate, 31, 58... 

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