Pentane-1,4-dioic acid

SYNS BOMYL DIMETHYL l,3-BIS(CARBOMETHO-XY)-l-PROPEN-2-YL PHOSPHATE DIMETHYL-1,3-DI(CARBOMETHOXY)-l-PROPEN-2-YL PHOSPHATE DIMETHYL 3-piMETHOXYPHOSPHINYLOXY)GLUTA-CONATE DIMETHYL 3-HYDROXYGLUTACONATE DIMETHYL PHOSPHATE ENT 24,833 FLY BAIT GRITS GC 3707 GENERAL CHEMICALS 3707 3-HYDROXYGLUTACONIC ACID, DIMETHYL ESTER, DIMETHYL PHOSPHATE 3-HYDROXY-2-PENTANE-DIOIC ACID, DIMETHYL ESTER, DIMETHYL PHOSPHATE PHOSPHORIC ACID, DIMETHYL ESTER, ESTER with DIMETHYL 3-HYDROXYGLUTACONATE... 

Wermuth, C.G., Mann, A., Schoenfelder, A., Wright, R.A., Johnson, B.G., etal. (1996) (2S,4S)-2-Amino-4-(4,4-diphenylbut-l-yl)-pentane-1,5-dioic acid a potent and selective antagonist for metabotropic glutamate receptors negatively linked to adenylate cyclase. J. Med. Chem. 39 814-816. 

CAS 110-94-1 El NECS/ELINCS 203-817-2 Synonyms Pentandioic acid Pentanedioic acid 1,5-Pentanedioic acid Pentane-1,5-dioic acid 1,3-Propanedicarboxylic acid... 

H02C(CH2)3C02H Glutaric acid Pentane-l,4-dioic acid 303... 

Unfortunately, the extraction and separation are not always complete. The situation just described, where components are perfectly soluble in one type of solvent and completely insoluble in another, is the exception rather than the norm. Most substances are somewhat soluble in both organic and aqueous solvents, even if the solubility in one of these is particularly low. This feature is illustrated by the following example. Consider the preparation of pentane-1,5-dioic acid from pentane-1,5-dinitrile according to the following reaction... 

If we were to perform an aqueous/organic extraction and separation at the end of this reaction, in which layer do you think that the product, pentane-1,5-dioic acid, will dissolve The structure of this organic acid has both polar (two carboxylic acid groups) and non-polar (hydrocarbon chain) parts, neither of which dominates the other, and the acid dissolves in both polar and non-polar solvents, and so some of the product would be in the organic layer and some would be in the aqueous layer. Obviously, this is not very helpful to the chemist who would like a clean separation of the product into one layer or the other. Although the case of this acid is an extreme example, this is not an entirely unusual occurrence. 

You should now be getting familiar with reading and understanding experimental procedures. Try and write an experimental and work-up procedure for the preparation of pentane-1,5-dioic acid from pentane-1,5-dinitrile. 

The experimental procedure for the preparation of pentane-1,5-dioic acid is illustrated schematically in Figure 2.1. 

Reflux a mixture of pentane-1,5-dinitrile (insert the number of g and mol to be used) and sulfuric acid (ml) in water (ml) for 10 hours and allow to cool. Using a separating funnel, extract the solution with ethoxyethane (4 x 150 ml portions). Dry the ethereal extracts with anhydrous magnesium sulfate. Distil off the ether to yield the desired product, pentane-1,5-dioic acid. 

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