Adipic aldehyde

Remove the catalyst by filtration at the pump, distil the solvent using a receiver for fractional distillation and collect the adipic aldehyde by distillation in a vacuum from a small flask fitted with a column. Yield 12-14 g. Pure adipic aldehyde boils at 92°-94°/12 mm., solidifies in an ice-salt freezing mixture and then melts at -8° to - 7°. Keep it in a sealed tube under nitrogen or C02 in order to protect it from auto-oxidation. 

Triphenylbismuth carbonate (2) displays remarkable chemoselecdvity, aUowing alcohol oxidation in the presence of benzenethiol, pyrrolidine, indole, aniline, dimethyl aniline and 3-pyrolidinocholesta-3,S-diene. The diol moiety in (3) is cleaved selectively without oxidizing the dithioacetal function (equation 3). The rate of the stoichiometric oxidative cleavage of ciJ-cyclohexane-l,2-diol to adipic aldehyde with Ph3BiC03 is faster than that of the trans isomer, suggesting the formation of a cyclic organobismuth intermediate (4 Scheme 1). ... 

Cyclic vicinal diols are split to dialdehydes or diketones, depending on the atoms or groups bonded to the carbons carrying the hydroxyls, dx-1,2-Cyclohexanediol and lead tetraacetate yield adipic aldehyde [446, 1155]. 

The stereochemistry of the diols often affects the yields of carbonyl compounds. Thus, the oxidation of cis-l,2-cyclohexanediol with sodium bismuthate in aqueous phosphoric acid and ether at 30 C gives only 23% of adipic aldehyde, whereas the trans isomer gives a 49% yield [483] (equation 303). 

Under a nitrogen atmosphere, 20 g (0.17 mol) of cis-l,2-cyclohexanediol is dissolved in 200 mL of dry benzene. Anhydrous potassium carbonate (50 g) is added, and the mixture is stirred vigorously while 76 g (0.17 mol) of lead tetraacetate is added in 5-g portions over a period of 1 h. After an additional hour of stirring, the mixture is filtered with suction, and the salts are extracted with benzene. The combined benzene solutions are dried over anhydrous sodium sulfate and evaporated in vacuo. The residue is distilled under a nitrogen atmosphere to give 13.4 g (68%) of colorless adipic aldehyde, bp 68-70 C at 3 mm of Hg. 

Synonyms Isododecanol Isolauryl alcohol Uses Antifoam coupling agent dispersant emollient emulsifier release agent solubilizer intermediate for sulfation, ethoxylation, esterification, phosphation, etc., for prod, of acrylates, adipates, aldehydes, alkyl ether sulfates, halides, alkyl phoshates, fatty acid esters, etc. 

The regioselective hydroformylation of conjugated and nonconjugated dienes has been reported. One example is the low-pressure 6w-hydroformylation of 1,3-butadiene 14 to adipic aldehyde The reaction yielded adipic aldehyde with 50% selectivity over 11 other possible products. The structure of the bisphosphite ligand had the largest effect on the selectivity of this reaction. 

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