Diethyl-ethanol

Synonyms 2,2-Diethyl ethanol 2EBO 2-Ethylbutanol 2-Ethyl butan-1-ol 2-Ethylbutanol-1... 

ChCl is choline chloride. Gly is glyceroL EG is ethylene glycoL MAc is malonic acid. EtjtElOHlNCl = N,N-diethyl ethanol ammonium chloride. 

Diethylenimide oxide. See Morpholine Diethyl ester, oxalic acid. See Diethyl oxalate N,N-Diethylethanamine. See Triethylamine Diethyl ethanedioate. See Diethyl oxalate 2,2-Diethyl ethanol. See 2-Ethyl-1-butanol... 

Synonyms 2,2-Diethyl ethanol 2EBO 2-Ethylbutanol 2-Ethyl butan-1-ol 2-Ethylb-utanol-1 2-Ethylbutyl alcohol s-Hexanol s-Hexyl alcohol 3-(Hydroxymethyl)-pentan 3-Methylolpentane 3-Pentylcarbinol s-Pentylcarbinol Pseudohexyl alcohol... 

CH3CH2OCH2CH2OH. A colourless liquid with a pleasant odour b.p. 135 C. Manufactured by heating ethylene oxide with ethanol and a catalyst, or by treating ethylene glycol with diethyl sulphate and sodium hydroxide. Used extensively as a solvent in nitrocellulose lacquers. 

C2He04S, Et0)(H0)S02. Oily acidic liquid. Soluble in water and slowly hydrolysed by it to ethanol and sulphuric acid. Prepared by passing ethene into concentrated sulphuric acid or by heating ethanol and sulphuric acid. Gives ethene when heated alone, and diethyl sulphate when heated with ethanol at 140 C. Forms crystalline metallic salts which are soluble in water. 

If the mixture contains an excess of ethanol, and is heated to 140°, the ethyl hydrogen sulphate reacts with the ethanol, giving diethyl ether And regenerating the sulphuric acid ... 

The crude product is evaporated to dryness and then heated with a mixture of ethanol and sulphuric acid the cyano group is thus hydrolysed giving malonic acid, which then undergoes esterification to give diethyl malonate. 

The diethyl ester which is precipitated rapidly solidifies on stirring. Filter it at the pump, wash with water (2 portions each of about 20 ml.), and recrystallise from methylated spirit or from 95% ethanol. Yield of pale yellow crystals, 8-9 g. m.p. 135-I37 ... 

Gently warm a mixture of 32 g. (32 ml.) of ethyl acetoacetate and 10 g. of aldehyde-ammonia in a 400 ml. beaker by direct heating on a gauze, stirring the mixture carefully with a thermometer. As soon as the reaction starts, remove the heating, and replace it when the reaction slackens, but do not allow the temperature of the mixture to exceed 100-no the reaction is rapidly completed. Add to the mixture about twice its volume of 2A -hydrochloric acid, and stir the mass until the deposit either becomes solid or forms a thick paste, according to the quality of the aldehyde-ammonia employed. Decant the aqueous acid layer, repeat the extraction of the deposit with more acid, and again decant the acid, or filter off the deposit if it is solid. Transfer the deposit to a conical flask and recrystallise it twice from ethanol (or methylated spirit) diluted with an equal volume of water. The i,4-dihydro-collidine-3,5-dicarboxylic diethyl ester (I) is obtained as colourless crystals, m.p. 130-131°. Yield 12 5 g,... 

Isopropanol has been used in the above experiment because it gives a greater yield of the phosphite than ethanol gives of diethyl hydrogen phosphite. The latter, b.p. 74 /i4 mm., can be prepared by replacing the isopropanol in the above experiment by 29 ml. (23 g.) of ethanol. 

The diethyl fumarate is readily prepared as follows. Reflux a mixture of 146 g. of fumaric acid (Section 111,143), 185 g. (236 ml.) of absolute ethanol, 450 ml. of boizene and 20 g. of concentrated sulphuric acid for 12 hours. Pour into a large volume of water, separate the benzene layer, wash successively with water, saturated lodium bicarbonate solution and water, dry with anhydrous magnesium sulphate, and remove the solvent on a steam bath. Distil the residue and collect the diethyl fumarate at 213-215° the yield is 150 g. 

Method B. Place 125 g. (106 -5 ml.) of diethyl phthalate and 25 g. of molecular sodium (sodium sand see Section 11,50,6) in a 500 ml. round-bottomed flask fitted with a reflux condenser and dropping funnel. Heat the flask on a steam bath and add a mixture of 122 5 g. (136 ml.) of dry ethyl acetate and 2 5 ml. of absolute ethanol over a period of 90 minutes. Continue the heating for 6 hours, cool and add 50 ml. of ether. Filter the sodium salt (VI) on a sintered glass funnel and wash it with the minimum volume of ether. Dissolve the sodium salt (96 g.) in 1400 ml. of hot water in a 3-htre beaker, cool the solution to 70°, stir vigorously and add 100 ml. of sulphuric acid (3 parts of concentrated acid to 1 part of... 

Note 2. Prepared by introducing gaseous HCl at -10°C into a mixture of 30 g of paraformaldehyde (corresponding to 1 mol of formaldehyde) and 1 mol of ethanol, until copious fumes escaped from the mixture. This was cooled (without stirring) to -70°C and the upper layer was decanted from the solid (frozen hydrochloric acid) and mixed with 50 g of yy-diethyl(or dimethyl)aniline. Subsequent distillation in a partial water-pump vacuum afforded the desired chloroether (b.p. about 40°C/40-50 mmHg). 

Ojj 1.5323, prepared from phenol, KOH in ethanol and propargyl bromide) was added and the mixture was heated at 60°C for 15 min. It was then poured into 200 ml of ice-water and the reaction products were extracted with diethyl ether. The ethereal extracts were washed with saturated NH Cl solution, dried over magnesium sulfate and then concentrated in a water-pump vacuum. There remained 9.5 g of 3 1 mixture... 

To a suspension of a tinc-copper couple in 150 ml of 100 ethanol, prepared from 80 g of zinc powder (see Chapter II, Exp. 18), was added at room temperature 0.10 mol of the acetylenic chloride (see Chapter VIII-2, Exp. 7). After a few minutes an exothermic reaction started and the temperature rose to 45-50°C (note 1). When this reaction had subsided, the mixture was cooled to 35-40°C and 0,40 mol of the chloride was added over a period of 15 min, while maintaining the temperature around 40°C (occasional cooling). After the addition stirring was continued for 30 min at 55°C, then the mixture was cooled to room temperature and the upper layer was decanted off. The black slurry of zinc was rinsed five times with 50-ml portions of diethyl ether. The alcoholic solution and the extracts were combined and washed three times with 100-ml portions of 2 N HCl, saturated with ammonium chloride. 

Diethyl oxalate (29.2 g, 0.20mol) and 4-bromo-2-nitrotoluene (21.6 g, O.lOmol) were added to a cooled solution of sodium cthoxide prepared from sodium (4.6 g, 0.20 mol) and ethanol (90 ml). The mixture was stirred overnight and then refluxed for 10 min. Water (30 ml) was added and the solution refluxed for 2h to effect hydrolysis of the pyruvate ester. The solution was cooled and concentrated in vacuo. The precipitate was washed with ether and dried. The salt was dissolved in water (300 ml) and acidified with cone. HCl. The precipitate was collected, washed with water, dried and recrystallizcd from hexane-EtOAc to give 15.2 g of product. 

Ethyl-4,5-thiazole dicarboxylates (77), R =H, Me, Et, Ph, or heteroaryl, were prepared from diethyl-a-chloro-/3-ketosuccinate (76) and thioamides in boiling ethanol (Scheme 35) (103, 110, 145, 298, 577, 639). 

Erlenmeyer et al. showed that it is possible to realize a moderated saponification of diethyl 4,5 thiazoledicarboxylate in mild conditions with an ethanolic potassium solution. The attack begins at the 5-position, and finally monoesters in the 4-position are obtained (Scheme 9) (17). 

These organometallic compounds cannot therefore be formed or used m solvents such as water and ethanol The most commonly employed sol vents are diethyl ether and tetrahydrofuran... 

When applied to the synthesis of ethers the reaction is effective only with primary alcohols Elimination to form alkenes predominates with secondary and tertiary alcohols Diethyl ether is prepared on an industrial scale by heating ethanol with sulfuric acid at 140°C At higher temperatures elimination predominates and ethylene is the major product A mechanism for the formation of diethyl ether is outlined m Figure 15 3 The individual steps of this mechanism are analogous to those seen earlier Nucleophilic attack on a protonated alcohol was encountered m the reaction of primary alcohols with hydrogen halides (Section 4 12) and the nucleophilic properties of alcohols were dis cussed m the context of solvolysis reactions (Section 8 7) Both the first and the last steps are proton transfer reactions between oxygens... 

On the basis of the mechanism for the acid catalyzed formation of diethyl ether from ethanol in Figure 15 3 write a stepwise mechanism for the formation of oxane from 1 5 pentanediol (see the equation on page 637)... 

The mechanism for the for mation of diethyl ether from ethanol under conditions of acid catalysis was shown in Figure 15 3... 

Sodium peroxide Glacial acetic acid, acetic anhydride, aniline, benzene, benzaldehyde, carbon di-sulflde, diethyl ether, ethanol or methanol, ethylene glycol, ethyl acetate, furfural, glycerol, metals, methyl acetate, organic matter... 

Reactions with Alcohols, Mercaptans, and Phenols. Alcohols add readily to acetaldehyde in the presence of trace quantities of mineral acid to form acetals eg, ethanol and acetaldehyde form diethyl acetal [105-57-7] (65). Similarly, cycHc acetals are formed by reactions with glycols and other polyhydroxy compounds eg, ethylene glycol [107-21-1] and acetaldehyde give 2-methyl-1,3-dioxolane [497-26-7] (66) ... 

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