Glutaconaldehyde, sodium salt

Glutaconaldehyde (8) 2-Pentenedial (9) (821-42-1) Glutaconaldehyde, sodium salt, dihydrate Glutaconaldehyde, ion (1 ) sodium (8) 2-Pentenedial, ion (1 ), sodium (9) (24290-36-6) Pyridinium-1-sulfonate Pyridinium, 1-sulfo-, hydroxide, inner salt (8,9) (42824-16-8)... 

FLUORIDE, 58, 75 Pyridinium-l-sulfonate, 59, 79 hydrolysis to glutaconaldehyde sodium salt, 59,79... 

GLUTACONALDEHYDE SODIUM SALT FROM HYDROLYSIS OF PYRIDINIUM-l-SULFONATE... 

The sodium and potassium salts of glutaconaldehyde are soluble only in polar solvents such as water, dimethyl sulfoxide, N,N-dimethylformamide, pyridine, and methanol. However, the stable tetrabutylammonium salt is soluble in relatively nonpolar solvents such as chloroform and ethyl acetate. It may be prepared from the potassium salt in the following manner. In a 1-1. Erlenmeyer flask equipped with a magnetic stirring bar are placed a solution of 13.6g. (0.1 mole) of crude glutaconaldehyde potassium salt in 200 ml. of water and a solution of 33.9 g. (0.1 mole) of tetrabutyl-ammonium hydrogen sulfate in 200 ml. of ice-cold water, the pH of wliich was adjusted to 10 by adding aqueous 2M sodium hydroxide. 

There are many examples of pyridinium salts, particularly, but not exclusively, those with powerful electron-withdrawing A-substituents, adding a nucleophile at C-2 and then undergoing a ring opening. The classic example is addition of hydroxide to the pyridine sulfur trioxide complex, which produces the sodium salt of glutaconaldehyde, as shown below. 

If an unsaturated dicarbonyl precursor is available, no oxidant needs to be added a synthesis of the perchlorate of pyrylium itself, shown below, falls into this category careful perchloric acid treatment of either glutaconaldehyde, or of its sodium salt, produces the parent salt. (CAUTION potentially explosive). 

Treatment of 1-pyridinium sulphonate with sodium or potassium hydroxide generates sodium or potassium salts of 5-hydroxy-2,4-pentadienal (glutaconaldehyde), which are starting materials for a variety of transformations (equation 178)171b 301. For example, the reaction of the potassium salt with a carbon electrophile has been used for the preparation of a dienol aldehyde (equation 179)mb which was an intermediate in the total synthesis of a mutagen, (S)-3-(dodeca-l,3,5,7,9-pentaenyloxy)propane-l,2-diol. 

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