Sodium ethylene glycolate

Interesting stereochemical aspects of the protic Bamford-Stevens reactions of the epimeric 7-oxohexa-hydrocannabinol tosylhydrazone acetates (70) and (72) have been recently demonstrated. When the axial epimer (70) was added to sodium ethylene glycol, the ring expansion product (71) was obtained in 38% yield. On the other hand, reaction of the equatorial epimer (72) under the same conditions yielded (73) in 56% yield (equations 45 and 46). Notably, the aprotic Bamford-Stevens reaction of the axial epimer (70) gave rise to (73) (30-40% yield) after acetylation. 

For the Bamford-Stevens reaction, smaller amounts of methyllithium or other bases, such as sodium alcoholates, LiH, NaH, sodium ethylene glycolate, or NaNH2 are used. The consequence is that the C — H group adjacent to the hydrazone moiety does not dissociate (2-35). Padwa et al. (1983 b) applied a similar process (2-36, NaH in THF) for the synthesis of the diazoalkene 2.82. 

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. 

C12H4CI4O2. A by-product in the preparation of 2,4,5-trichlorophenol from 1,2,4,5-tetrachlorobenzene, sodium hydroxide and ethylene glycol. Causes chloracne in humans. 

Sodium me/aperiodate (NalO ) in cold aqueous solution readily oxidises 1,2-diols with splitting of the molecule and the consequent formation of aldehydes or ketones thus ethylene glycol gives formaldehyde and pinacol gives acetone. In the case of a 1,2,3-triol, the central carbon atom of the triol... 

Polyhydric alcohols are compounds containing two or more hydroxyl groups in the molecule. The two most important are ethylene glycol HOCHjCHjOH (a dihydric alcohol) and glycerol HOCHjCH(OH)CH. OH (a trihydric alcohol). Ethylene glycol may be obtained by the hydrolysis of ethylene dibromide or ethylene dichloride with dilute aqueous sodium hydroxide or sodium carbonate solution ... 

Chapter III. 1 Heptene (111,10) alkyl iodides (KI H3PO4 method) (111,38) alkyl fluorides (KF-ethylene glycol method) (111,41) keten (nichrome wire method) (111,90) ion exchange resin catalyst method for esters (111,102) acetamide (urea method) (111,107) ethyl a bromopropionate (111,126) acetoacetatic ester condensation using sodium triphenylmethide (111,151). 

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... 

Many industrial processes have been employed for the manufacture of oxahc acid since it was first synthesized. The following processes are in use worldwide oxidation of carbohydrates, the ethylene glycol process, the propylene process, the diaLkyl oxalate process, and the sodium formate process. 

A provocative reaction of ethylene glycol direcdy with siUcon dioxide that leads to a complex mixture of oligomeric and cycHc ester species has been reported (32). This reaction proceeds in the presence of sodium hydroxide or in the presence of high boiling tertiary amines (33). 

The addition product, C QHgNa, called naphthalenesodium or sodium naphthalene complex, may be regarded as a resonance hybrid. The ether is more than just a solvent that promotes the reaction. StabiUty of the complex depends on the presence of the ether, and sodium can be Hberated by evaporating the ether or by dilution using an indifferent solvent, such as ethyl ether. A number of ether-type solvents are effective in complex preparation, such as methyl ethyl ether, ethylene glycol dimethyl ether, dioxane, and THF. Trimethyl amine also promotes complex formation. This reaction proceeds with all alkah metals. Other aromatic compounds, eg, diphenyl, anthracene, and phenanthrene, also form sodium complexes (16,20). 

Ethylenediamine (70,71), benzyl alcohol and acetone (72), ethylene glycol (73) and C2—C g carboxyUc acids (74) are claimed to increase the reactivity of cellulose toward acetylation. Sodium hydroxide and Hquid ammonia (71) are excellent swelling agents and have been used to activate cellulose before esterification. Ultrasonic treatment of cellulose slurries (75) reportedly swells the fibers and improves reactivity. 

The formation of acetals with methanol, ethanol, or ethylene glycol in the presence of an acid catalyst such as hydrogen chloride or ben2enesulfonic acid is straightforward. Sodium bisulfite and hydroxjlamine form adducts with cinnamaldehyde that are used in typical quantitative analysis protocols. 

With Phenols. The 2-hydroxylethyl aryl ethers are prepared from the reaction of ethylene oxide with phenols at elevated temperatures and pressures (78,79). 2-Phenoxyethyl alcohol is a perfume fixative. The water-soluble alkylphenol ethers of the higher poly(ethylene glycol)s are important surface-active agents. They are made by adding ethylene oxide to the alkylphenol at ca 200°C and 200—250 kPa (>2 atm), using sodium acetate or... 

Has been purified by co-distillation with ethylene glycol (boils at 197.5°), from which it can be recovered by additn of water, followed by crysm from 95% EtOH, benzene, toluene, a mixture of benzene/xylene (4 1), or EtjO. It has also been chromatographed on alumina with pet ether in a dark room (to avoid photo-oxidation of adsorbed anthracene to anthraquinone). Other purification methods include sublimation in a N2 atmosphere (in some cases after refluxing with sodium), and recrystd from toluene [Gorman et al. J Am Chem Soc 107 4404 1985]. 

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