Adipic acid ethyl ester

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

An oven-dried 100 ml flask with a side arm dosed with a septum is fitted with a magnetic stirring bar and a reflux condenser connected to a mercury bubbler. The flask is cooled to room temperature under nitrogen, charged with 4.36 g (0.025 mol) of adipic acid monoethyl ester followed by 12.5 ml of anhydrous tetrahydrofuran, and cooled to —18° by immersion in an ice-salt bath. Then 10.5 ml of 2.39 m (or 25 ml of 1 m) solution of borane in tetrahydrofuran (0.025 mol) is slowly added dropwise over a period of 19 minutes. The resulting clear reaction mixture is stirred well and the ice-salt bath is allowed to warm slowly to room temperature over a 16-hour period. The mixture is hydrolyzed with 15 ml of water at 0°. The aqueous phase is treated with 6 g of potassium carbonate (to decrease the solubility of the alcohol-ester in water), the tetrahydrofuran layer is separated and the aqueous layer is extracted three times with a total of 150 ml of ether. The combined ether extracts are washed with 30 ml of a saturated solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 3.5 g (88%) of a colorless liquid which on distillation yields 2.98 g (75%) of ethyl 6-hydroxyhexanoate, b.p. 79°/0.7 mm. 

CAS 141-28-6 EINECS/ELINCS 205-477-0 Synonyms Adipic acid, diethyl ester Diethyl adipatate Diethyl hexanedioate 1,6-Diethyl hexanedioate Ethyl adipate Ethyl 5-carboethoxyvalerate Hexanedioic acid, diethyl ester Empirical C10H18O4 Formula (-CH2CH2COOC2H5)2 Properties Colorless liq. sol. in alcohol, many other org. soivs. insol. in water m.w. 202.25 sp.gr. 1.009 m.p. -18 C b.p. 240-251 C flash pt. (CC) > 100 C ref. index 1.427 (20 C)... 

Selective reduction. A soln. of borane in tetrahydrofuran added dropwise at -18 during 19 min. to a mixture of adipic acid monoethyl ester and tetrahydrofuran, stirred and allowed to warm to room temp, during 16 hrs. -> ethyl 6-hydroxy-hexanoate. Y 75-88%. - Other functional groups such as cyano, halogeno, keto, or nitro, are likewise retained during this highly convenient reduction. F. e., also reduction of sterically hindered acids, s. N. M. Yoon, H. C. Brown et al., J. Org. Chem. 38, 2786 (1973) 2-aminoalcohols from a-aminocarboxylic acids s. M. L. Anhoury et al., Soc. Perkin 11974,191 via reduction with aq. NaBH of enolesters obtained from the acids and N-ethyl-5-phenylisoxazolium 3 -sulfonate (s. Synth. Meth. 16, 448) s. P. L. Hall and R. B. Perfetti, J. Org. Chem. 39, 111 (1974). 

Acrylic Acid Ethyl Ester Ethyl Acrylate Ethyl Propenoate Diisobutyl Adipate Butyl Acrylate... 

The above example serves to iUustrate the basis of the procedure employed for the characterisation of aUphatic esters, viz., hydrolysis to, and identification of, the parent acids and alcohols. Most esters are liquids a notable exception is dimethyl oxalate, m.p. 54°. Many have pleasant, often fruit-hke, odours. Many dry esters react with sodium, but less readily than do alcohols hydrogen is evolved particularly on warming, and a sohd sodio derivative may separate on coohng (e.j/., ethyl acetate yields ethyl sodioacetoacetate ethyl adipate gives ethyl sodio cj/cZopentanone carboxylate). 

This method with some slight modihcations is applied in the synthesis of to-bromo esters from Cs to Cn. Methyl 5-bromovalerate has been prepared by treating the silver salt of methyl hydrogen adipate with bromine. The ethyl ester has been prepared from the acid by esterification or through the acid chloride. ... 

NITRO-, ETHYL ESTER, ( >], 65 Adipic acid [Hexanedioic acid], 70 DL-Alanine, jV-(tnfluoroacetyl)-, 125 Alcohols, primary, 40... 

A solution of borane in tetrahydrofuran reduces esters at room temperature only slowly [977]. Under such conditions free carboxylic groups of acids are reduced preferentially monoethyl ester of adipic acid treated with 1 mol of borane in tetrahydrofuran at — 18° to 25° gave 88% yield of ethyl 6-hydroxy-hexanoate [977]. Borane-dimethyl sulfide in tetrahydrofuran was used for... 

In dicarboxylic acids with one free and one esterified carboxyl group the free carboxyl only may be reduced with hydrides (alanes, boranes). The monoethyl ester or adipic acid was converted by an equimolar amount of borane in tetrahydrofuran at —18° to 25° to ethyl 6-hydroxyhexanoate in 88% yield [971] Procedure 19, p. 209). 

Hydroxymethylfurfural may be oxidized to 5>hydroxymethyl-furan-2-carboxylic acid (LV), the ethyl ester of which is easily hydrogenated to ethyl 5-hydroxymethyltetrahydrofuran-2-carboxylate (LVI). This ester is a potential source of adipic acid by the following series of... 

Thermoset polymeric esters consisting of neopentyl glycol, propylene glycol, trimethylol propane, adipic acid, maleic anhydride, and 2-ethyl hexanol were prepared by McAlvin et al. (3) and were used in blends containing styrene monomer. The mixture was cured by pultrusion and had improved weatherabil-ity characteristics. 

Ethyl hydrogen adipate and ethyl hydrogen sebacate may be converted to the corresponding ester acid chlorides by this procedure in about the same yields. Distillation should be carried out rapidly at a pressure of 4 mm. or lower. 

Sipalin AOM. Ger trade name for the methyl-cyclohexyl ester of adipic acid. It was incorporated in solvents for NC (such as 75/25 butyl acetate/ethyl ale), the soln being used to coat electric detonator fuseheads by a dipping procedure. The Sipalin resulted in a NC varnish coating which was less permeable to moisture and less readily cracked... 

Adipic Acid.—The ethyl potassium salt was converted into the sebaeic diethyl ester by Brown and Walker1 ... 

Acetyl-n-valeric acid has been prepared by the oxidation of 1-methylcyclohexene with potassium permanganate 5 by the oxidation of 2-methylcyclohexanone with chromic oxide and sulfuric acid 6 by the reaction of methylzinc iodide on the ethyl ester of adipic acid chloride and saponification of the ethyl ester of 5-acetyl-w-valeric acid so obtained 7 by the saponification of the ethyl ester of diacetylvaleric acid 2 and through the hydrolysis of ethyl a-acetyl-6-cyanovalerate with boiling 20% hydrochloric acid.3... 

SYNS ADIPIC ACID, BIS(2-ETHOXYETHYL) ESTER DIETHOXY ETHYL ADIPATE HEXANOIC ACID, BIS(2-ETHOXYETHYL) ESTER... 

In the second step, the olefmic ester is sent to another reactor with a new quantity of carbon monoxide and methanol. The operation takes place at high temperature, 185°C, hut at lower pressure (3. IQ6 Pa absolute). Methyl adipate is formed with a molar yield of 75 per cent Methyl glutarate and methyl ethyl succinate are also formed. After purification by distillation, the methyl adipate is hydrolysed to adipic acid. 

In 1887, Claisen and Lowman reported that the condensation of 2 mol of an ester, such as ethyl acetate, in the presence of base gave the p-keto ester, ethyl acetoacetate (ethyl 3-oxobutanoate equation 1). The intramolecular equivalent was recognized by Dieckmann in 1894. He found that heating an adipic acid ester with sodium and a trace of alcohol led to cyclization, with the formation of a cyclopentanone (equation 2). The reaction was, at an early stage, extended to the acylation of ketones. Claisen himself reported the base-catalyzed reaction of acetophenone and ethyl benzoate to give dibenzoylmethane in 1887. This reaction, too, has an intramolecular parallel. The acylation of ketones with esters and other acid derivatives is sometimes called a Claisen condensation, although this usage is criticized by some writers and avoided by others. A widely used example of ketone acylation is the synthesis of a-formyl (hydroxymethylene) ketones (equation 3). Intramolecular variants of this reaction include the classical synthesis of dimedone (Scheme 1). 

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