Diethyl adipate hexanedioate

It may also help to distil out the water that is formed in the reaction diethyl adipate (the diethyl ester of hexanedioic add) can be made in toluene solution using a sixfold excess of ethanol, concentrated H2SO4 as catalyst, distilling out the water using a Dean Stark apparatus. You can tell from the yield that the equilibrium is very favourable. 

Suggest mechanisms for these reactions, commenting on the choice of reagents and solvents. How would you convert the final product into diethyl hexanedioate [diethyl adipate, Et02C(CH2)4C02Et] ... 

Adipic acid, diethyl ester. See Diethyl adipate Adipic acid, dihexyl ester. See Dihexyl adipate Adipic acid dihydrazide CAS 1071-93-8 EINECS/ELINCS 213-999-5 Synonyms Adipic dihydrazide Adipodihydrazide Adipoyl hydrazide Hexanedioic acid, dihydrazide Ciassification Nonaromatic amide hydrazide Definition Reaction prod, of hydrazine and adipic acid... 

Diethyl-2,6-heptadienal 2,4-Diethylhepta-2,6-dienal 2,4-Diethyl-2,6-heptadienal, mixture of isomers. See Diethylheptadienal Diethyl hexanedioate 1,6-Diethyl hexanedioate. See Diethyl adipate... 

Hexanedioic acid, diethyl ester. See Diethyl adipate... 

An intramolecular Claisen condensation of a dicarboxylic ester to give a five- or six-membered ring is known as a Dieckmann condensation. In the presence of one equivalent of sodium ethoxide, diethyl hexanedioate (diethyl adipate), for example, undergoes an intramolecular condensation to form a five-membered ring ... 

Just as there is an intramolecular version of the aldol condensation (see Section 22.2), there is an intramolecular version of the Claisen condensation. A simple illustration is treatment of an a,(0-diester such as diethyl 1,6-hexanedioate (77, the diethyl ester of adipic acid called diethyl adipate see Chapter 20, Section 20.9) with sodium ethoxide in refluxing ethanol. When this experiment is done, triphenylmethide (19 introduced in Section 22.1) is used as the base, and reaction in the solvent benzene gives the isolated flnal product (86) in 70% yield. Note that benzene is rarely used now-a-days because it is a suspected carcinogen and its use is being phased out. This reaction sequence uses the same mechanism as the Claisen condensation. 

Intramolecular acylations often go very well indeed when a five- or a six-membered ring is being formed, A classic case is the cyclization of the diethyl ester of adipic acid (diethyl hexanedioate), a component in nylon manufacture. 

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)... 

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