Sodium phenyl acetate

To a well stirred suspension of 9 g of sodium phenyl acetate and 2.4 g of magnesium turnings in 25 cc of anhydrous ether, a solution of 9.4 cc of isopropyl bromide in 50 cc of anhydrous ether are added. The mixture is refluxed for one hour (during which time propane is evolved) and then 5 cc of cyclopentanone in 25 cc of anhydrous ether are added dropwise. The mixture is then refluxed for one hour and poured over ice water containing some hydrochloric acid. The ether solution is separated and extracted with 200 cc of 5% sodium hydroxide. The alkaline solution on acidification gives the free acid which is filtered off, dried in a desiccator and recrystallized from a mixture of ethylene dichloride and petroleum ether. 

PHENYL ACETIC ACID SODIUM PHENYL ACETATE 4.3 3.5 to 5.1... 

To hydrolyse an ester of a phenol (e.g., phenyl acetate), proceed as above but cool the alkaline reaction mixture and treat it with carbon dioxide until saturated (sohd carbon dioxide may also be used). Whether a solid phenol separates or not, remove it by extraction with ether. Acidify the aqueous bicarbonate solution with dilute sulphuric acid and isolate the acid as detailed for the ester of an alcohol. An alternative method, which is not so time-consuming, may be employed. Cool the alkaline reaction mixture in ice water, and add dilute sulphuric acid with stirring until the solution is acidic to Congo red paper and the acid, if aromatic or otherwise insoluble in the medium, commences to separate as a faint but permanent precipitate. Now add 5 per cent, sodium carbonate solution with vigorous stirring until the solution is alkaline to litmus paper and the precipitate redissolves completely. Remove the phenol by extraction with ether. Acidify the residual aqueous solution and investigate the organic acid as above. 

However, this method is appHed only when esterification cannot be effected by the usual acid—alcohol reaction because of the higher cost of the anhydrides. The production of cellulose acetate (see Fibers, cellulose esters), phenyl acetate (used in acetaminophen production), and aspirin (acetylsahcyhc acid) (see Salicylic acid) are examples of the large-scale use of acetic anhydride. The speed of acylation is greatiy increased by the use of catalysts (68) such as sulfuric acid, perchloric acid, trifluoroacetic acid, phosphoms pentoxide, 2inc chloride, ferric chloride, sodium acetate, and tertiary amines, eg, 4-dimethylaminopyridine. 

A related agent, g1 icetanile sodium (42), is made b / a variant of this process. Methyl phenyl acetate is reacted with chlorosulfonic acid to give 38, which itself readily reacts with aminopyrimidine derivative 39 to give sulfonamide Saponification to acid 4 is followed by conversion to the acid chloride and amide formation with 5-chloro-2-methoxyaniline to complete the synthesis of the hypoglycemic agent glicetanile (42). ... 

Phenyl-ethyl alcohol can be prepared by numerous methods, several of which are the subject-matter of patents. It may be prepared, for example, by the conversion of phenyl-bromo-lactic acid into phenyl-acetaldehyde, and then reducing this body with sodium. Or it may be prepared by reducing phenyl-acetic esters with sodium and absolute alcohol in the folio-wing manner —... 

To a solution of 4 g of sodium in 200 ml of n-propanol is added 39 g of homovanillic acid-n-propyl ester (boiling point 160°C to 162°C/4 mm Hg) and the mixture is concentrated by evaporation under vacuum. After dissolving the residue in 200 ml of dimethylformamide and the addition of 0.5 gof sodium iodide, 26.2 g of chloracetic acid-N,N-diethylamide are added drop-wise with stirring at an internal temperature of 130°C, and the mixture is further heated at 130°C for three hours. From the cooled reaction mixture the precipitated salts are removed by filtering off with suction. After driving off the dimethylformamide under vacuum, the product is fractionated under vacuum, and 44.3 g of 3-methoxy-4-N,N-diethylcarbamido-methoxy phenyl acetic acid-n-propyl ester are obtained as a yellowish oil of boiling point 210°C to 212°C/0,7 mm Hg,... 

Preparation of 3 5-diiodo-4-(4 -hydroxyphenoxy)phenylacetic acid (diac) A solution of ethyl 3 5-diiodo-4-(4 -methoxyphenoxy)phenyl acetate (9.5 g) in acetic acid (60 ml) was heated under reflux with hydriodic acid (SG 1.7, 50 ml) and red phosphorus (0.5 g) for 1 hour. The hot solution was filtered and the filtrate concentrated at 50°C and 15 mm of mercury to above 20 ml. The residue was treated with water (70 ml) containing a little sodium thiosulfate to decolorize the product. The solid was collected by filtration and purified by the method of Harington and Pitt-Rivers [Biochem. J. (1952), Vol. 50, page 438]. Yield 8,36 g (95%). After crystallization from 70% (v/v) acetic acid it melted at 219°C. 

A suspension of sodium amide2 (0.1 mole) in liquid ammonia is prepared in a 500-ml. three-necked, round-bottomed flask fitted with a West condenser, a ball and socket glass mechanical stirrer (Note 1), and a dropping funnel. In the preparation of this reagent a small piece of clean sodium metal is added to 350 ml. of commercial anhydrous liquid ammonia. After the appearance of a blue color, a few crystals of hydrated ferric nitrate are added, whereupon the blue color is discharged. The remainder of the 2.3 g. (0.1 mole) of sodium (Note 2) is then rapidly added as small pieces. After all the sodium has been converted to sodium amide (Note 3), a solution of 16.4 g. (0.1 mole) of ethyl phenyl-acetate (Note 4) in 35 ml. of anhydrous ethyl ether is added dropwise over a 2-minute period, and the mixture is stirred for 20 minutes. To the dark green suspension is added over an 8-minute period a solution of 18.5 g. (0.1 mole) of (2-bromo-... 

Sebacic acid, 43, 39 Sebacoyl chloride, 43, 37 2,2 -SebacoyldicycIohexanone, 43, 34 Silver difluoride, reaction with phenyl disulfide, 44, 82 Silver monofluoride, 44, 82 Sodium amide, as catalyst for carbona-tion of methylacetylene, 42, 98 for formation of sodium sodiophenyl-acetate, 40, 38... 

Trace amounts of bromine in sodium diclofenac, sodium (2-[(2, 6-dichlorophenyl)amino] phenyl acetate, have been determined using XRF [82], since the drug substance should not contain more than 100 ppm of organic bromine remaining after the completion of the chemical synthesis. Pellets containing the analyte were compressed over a boric acid support, which yielded stable samples for analysis, and selected XRF spectra obtained in this study are shown in Fig. 7.19. It was found that samples from the Far East contained over 4000 ppm of organic bromine, various samples from Europe contained about 500 ppm, while samples from an Italian source contained less than 10 ppm of organic bromine. 

The easily available 1-bromo-l-seleno alkene, by treatment with sodium phenyl tellurolate under bis(bipyridine)nickel (11) bromide catalysis, furnishes the corresponding telluro(seleno)ketene acetal. " ... 

Phenylacetamide has been obtained by a wide variety of reactions from benzyl cyanide with water at 250-260° 6 from benzyl cyanide with water and cadmium oxide at 240° 6 from benzyl cyanide with sulfuric acid 7 8 by saturation of an acetone solution of benzyl cyanide with potassium hydrosulfide 9 from benzyl cyanide with sodium peroxide 10 by electrolytic reduction of benzyl cyanide in sodium hydroxide 11 from ethyl phenyl-acetate with alcoholic 12 or aqueous 13 ammonia from phenyl-acetic acid with ammonium acetate 14 or urea 15 from diazoacetophenone with ammoniacal silver solution 16 from phenyl-acetic acid imino ether hydrochloride and water 17 from acetophenone with ammonium poly sulfide at 215° 18 from benzoic acid 19 and by heating the ammonium salt of phenyl-acetic acid.20... 

Treatment of the dibromides with sodium ethoxide gives 2-bromo-methyl-2,3-dihydrobenzofurans (170) o- (2,3-dibromopropyl)phenyl acetate (188, X = OAc, R = H) gives 2-bromomethyl-2,3-dihydro-benzofuran (170, R = R1 = H).447 The following substituted 2-bromo-methyl-2,3-dihydrobenzofurans have been prepared by this method ... 

Optional) Prevent microbial growth by placing a test tube or small bottle containing toluene, sodium azide, phenyl acetate, or thymol (for non-fatty products) inside the closed chamber to prevent mold growth on the sample at aw>0.75. 

CAUTION Sodium azide (NaN3) and phenyl acetate are poisonous. Toluene is not recommended since it is carcinogenic. Take appropriate precautions when using any of these chemicals. See appendix 2B for more information. 

Sodium phenyl phosphate substrate acetate buffer, pH 5 30 min at 37°. Activity expressed as units (i.e., mg P/30 min/100 ml enzyme solution). 

Sodium Acetic anhydride Phenyl acetate Sodium... 

Ozonolysis of vinylpyrazine in methanol at — 30° furnishes pyrazine aldehyde in 73% yield.196 Vinylpyrazine undergoes a variety of addition reactions and pyrazylethyl derivatives of amines, ketones, ethyl phenyl acetate, phenylacetonitrile, and acetamide have been obtained.197-199 2-(2-Pyrazylethyl)cyclohexanone (42) has been prepared both by the condensation of vinylpyrazine with cyclohexanone in the presence of sodium metal and by interaction of vinylpyrazine with the pyrrolidine enamine of cyclohexanone followed by hydrolysis.200... 

The mechanism of the Montedison reaction has been studied in some detail, and tentative mechanisms have been offered. The proposed catalytic cycle is shown in Fig. 4.11. The biphasic reaction medium consists of a layer of diphenyl ether and that of aqueous alkali. In the presence of alkali, the precatalyst Co2(CO)8 is converted into 4.7. The sodium salt of 4.7 is soluble in water but can be transported to the organic phase, that is, a diphenyl ether layer by a phase-transfer catalyst. The phase-transfer catalyst is a quaternary ammonium salt (R4N+X ). The quaternary ammonium cation forms an ion pair with [Co(CO)4]. Because of the presence of the R groups, this ion pair, [R4N]+[Co(CO)4], is soluble in the organic medium. In the nonaqueous phase benzyl chloride undergoes nucleophilic attack by 4.7 to give 4.40, which on carbonylation produces 4.41. The latter in turn is attacked by hydroxide ion transported from the aqueous phase, to the organic phase again by the phase-transfer catalyst. The product phenyl acetate and 4.7 are released in the aqueous phase as the sodium or quaternary ammonium salts. 

Insoluble Sodium Metaphosphate, 52 Insoluble Sodium Polyphosphate, 52 Isoamyl Alcohol, 78 Isoamyl Benzoate, 78 Isoamyl Butyrate, 78 Isoamyl Phenyl Acetate, 78 Isoamyl Salicylate, 78 Isobutyl Cinnamate, 78 Isobutyl Isovalerate, 84 Isobutyraldehyde, 78 DL-Isoleucine, 30 L-Isoleucine, 31 Isopropyl Acetate, 80... 

---