Acetic acid ethyl ester solvent

A stirred mixture of 11 g of 6-chloro-a-methylcarbazole-2-acetic acid ethyl ester, 100 ml ethanol and 100 ml of 3N sodium hydroxide was heated (N2 atmosphere). After 2 hours at reflux, the reaction mixture was concentrated to dryness under reduced pressure. Water (300 ml) and ice (200 g) were added to the residue and concentrated hydrochloric acid was added until the mixture was strongly acid. The acidic mixture was extracted with ether (3 X 200 ml). The ether extracts were combined, washed by extraction with water (3 x 100 ml) and dried over anhydrous magnesium sulfate. Following filtration of the desiccant and evaporation of the solvent, a yield of 9.8 g (98.2%) was obtained. Crystallization from CHCI3 yielded 6.2 g (62.0%) of 6-chloro-0 -methylcarbazole-2-acetic acid, MP 197°-198°C. A second crop of 1.6g,MP 195°-199°C was obtained from the mother liquors. 

After having been washed with 50 cc of water the benzene layer is dried over potassium carbonate, filtered, allowed to stand over 10 g of alumina for about VA hours for partial decolorization, filtered again and concentrated under reduced pressure. The oily base which remains as a residue is directly converted into the tartrate. A solution cooled to 0°C, of 6.50 g of the free base in 100 cc of acetic acid ethyl ester is thoroughly shaken and poured into an ice cold solution of 2.66 g of tartaric acid in 410 cc of acetic acid ethyl ester. The precipitated, analytically pure, tartrate of 3-methylsulfinyl-10-[2 -N-methyl-piperidyl-2")-ethyl-1 ]-phenothiazine melts at 115° to 120°C (foam formation) and sinters above B0°C. The base Is reacted with benzene sulfonic acid in a suitable solvent to give the besylate. 

Note Polar solvent soluble in water, alcohols (organic halides), ether, and many oils flammable moderately toxic by inhalation and skin absorption incompatible with strong oxidizers, nitrates, strong alkalis, strong acids. Synonyms acedin, acetic ether, acetic ester, ethyl ethanoate, vinegar naphtha, acetic acid ethyl ester. 

In the main esterification process for acetic acid ethyl ester (ethyl acetate) a mixture of acetic acid and ethanol with a small amount of sulphuric acid is preheated and fed to an esterifying column where it is refluxed. The mixture removed goes to a second refluxing column where a ternary azeotrope containing 85% ethyl acetate is removed. Water is mixed with the distillate after which it separates into two layers. The top layer is fed to a refluxing column from which the residue containing 95% ethyl acetate is distilled to remove any impurities. Ethyl acetate and ethyl lactate are used as solvents. Some ethyl esters of carboxylic acids are used as flavor and aroma substances. 

S g of ethyl glycinate hydrochloride were dissolved in 400 cc of ethanol and 33.5 g of salicylic aldehyde were added. It is refluxed for half an hour and cooled. 38 cc of triethylamlne and 25 g of Raney nickel are then added whereafter hydrogenation is carried out at room temperature and under atmospheric pressure. After hydrogen adsorption was complete, the mixture was filtered and the alcohol evaporated off. The residue was taken up with acidified water, extracted with ether to eliminate part of the by-products, consisting mainly of o-cresol, then made alkaline with ammonia and extracted with ethyl acetate. The solvent was removed in vacuo and the residue crystallized from ether/petroleum ether. 36.7 g of o-hydroxybenzyl-aminoacetlc acid ethyl ester melting at 47°C are obtained. 

The potassium salt of ethyl o-nitrophenylpyruvate is prepared essentially according to the method of Wislicenus and Thoma.14 However, the isolation of ethyl o-nitrophenylpyruvate has been eliminated by liberating the ester from its potassium salt in the acetic acid used as solvent for the hydrogenation. Catalytic... 

As a chemical raw material, ethanol is used for the production of a range of monomers and solvents, and is essential in pharmaceutical purification. In the presence of an acid catalyst ethanol reacts with carboxylic acids to produce ethyl esters. The two largest-volume ethyl esters are ethyl acrylate (from ethanol and acrylic acid) and ethyl acetate (from ethanol and acetic acid). Ethyl acrylate is a... 

HN C6H.6N( 0)2 mw 126.12, plates (from, w), mp 300° (dec) si sol in ale hot w insol in usual solvents. Prepd by boiling with soda soln jS-hydroxy/3-amino-glutaric acid ethyl ester amide, or by heating at 130°2,4 6-trihydroxypyridine and ammonium acetate... 

A solution of 57.0 g (0.12 mole) of [[2-methyl-l-(l-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetic acid, phenyl methyl ester in 300 ml of ethyl acetate was treated with 3.0 g of 10% Pd/C and hydrogenated on the Parr apparatus (45 psi) for 4 hours. The mixture was filtered through Hyflo and the solution was extracted with 5% NaHC03. The aqueous extracts were washed with ether, cooled to 5°C and treated with 36 ml of HOAc. The product was extracted into ethyl acetate, dried (MgS04) and the solvent was evaporated in vacuo. The residue was dissolved in 300 ml of toluene and the solvent was evaporated in vacuo to remove last traces of acetic acid. The oil residue became semi-solid on standing at room temperature. The yield of the product of debenzoylation - 2-[carboxymethyl)-(4-phenylbutyl)-phosphinoyloxy]-2-methylpropionic acid ethyl ester (racemic mixtures) was 39.8 g (72%). 

A stirred suspension of 5 g of (S)-5-(2-oxo-l,3-oxazolidin-4-ylmethyl)-3-[(2-toluen-4-sulphoniloxy)ethyl]-lH-indol-2-carboxylic acid ethyl ester in 30 ml of a 2 N solution of dimethylamine in ethanol was stirred at 50°C for 20 hours in a closed reactor. The solvent was evaporated to dryness, the residue dissolved in 20 ml of 2 N HCI and washed three times with 15 ml of dichloromethane. The washed aqueous phase was cooled and adjusted to pH 12 with a 40% sodium hydroxide solution and extracted three times with 20 ml of dichloromethane. The combined organic phases were washed with brine and dried above anhydrous sodium sulphate. The solvent was evaporated to dryness and the residue recrystallised from ethyl acetate to give 3.4 g (91%) of the title dimethylamine as a yellow solid. Melting point 67°-70°C. 

To a solution of 1.4 g (24.9 mmoles) of KOH in 10 ml of ethanol was added 2.8 g (7.8 mmoles) of (S)-3-(2- dimethylaminoethyl)-5-[2-oxo-l,3-oxazolidin-4-ylmethyl]-lH-indol-2-carboxylic acid ethyl ester. The resulting solution was heated at reflux temperature for one hour. It was cooled and the solvent evaporated to dryness. The residue was dissolved in 6 ml of water and washed three times with 10 ml of dichloromethane. The aqueous solution was cooled to 5°C, adjusted to pH 6 with glacial acetic acid, stirred for 30 minutes at that temperature and the water evaporated to dryness. The residue was redissolved in 30 ml of water and 5 g of ionic exchange resin (Dowex50WX8-400) added. The mixture was left under stirring at room temperature for 24 hours. The resin was filtered and it was washed with water. For desorbtion the resin was suspended with 20 ml of a 10% aqueous solution of ammonia and stirred at room temperature for 5 hours. After that it was filtered and washed with water, water was evaporated to dryness under reduced pressure to give 7.75 g (94%) of the title acid as a yellow crystalline solid. Melting point 230°C. 

In a third microreactor, the anion of 4-ferf-butyl l-ethyl-2-(diethox-yphosphoryl)succinate was prepared in situ using sodium ethoxide 237 (in EtOH) and the Wittig-Horner olefination with benzaldehyde 116 performed using a residence time of 47 min to afford (E)-ferf-butyl-l-ethyl-2-benzylidenesuccinate 238 in excellent selectivity (89% yield). In a fourth reactor, the acid-catalyzed (TFA 239) ferf-butyl ester deprotection was achieved using a residence time of 5 min at 34 °C and employing DCM as the reaction solvent to afford (E)-3-(ethoxycarbonyl)-4-phenylbut-3-enoic acid 246 in 82% yield. The deprotection was subsequently followed by a Friedel-Crafts acylation, using triethylamine 14 and acetic anhydride 37, to afford 4-acetoxy-naphthalene-2-carboxylic acid ethyl ester 241 in quantitative yield when conducted at 130 °C (residence time = 47 min). 

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