tert-Butyl esters of aliphatic dibasic acids was written by Backer, H. J.;Homan, J. D. H.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1939.Name: Di-tert-butyl decanedioate The following contents are mentioned in the article:
Di-tert-Bu esters (I) of aliphatic dibasic acids with an even number of C atoms (up to sebacic) have higher m. ps. than the neighboring odd-numbered acids. I also have higher m. ps. than the corresponding Me and Et esters with the single exception of MeO2C(CH2)8CO2Me. The striking oscillation in the m. ps. of I is apparent in the following series of m. ps. of the esters from the oxalate (II) to the sebacate (III) resp.: 71掳, -7掳, 36掳, -10掳, 32.5掳, -15掳, 29掳, -18掳, 18掳. Two general methods were followed in the preparation of the esters, the 1st, using C5H5N as catalyst, the 2nd Me2NPh (IV). The acid chlorides (0.2 mol.) in 2 volumes of anhydrous C6H6 are added dropwise to 1 mol. Me3COH (V) (dried over Na) in 0.6 mol. C5H5N (distilled over KOH). The reaction mixture is agitated and maintained below 50掳. Upon completion of the 1st stage the solution is heated in a water bath for 3 hrs., cooled and the precipitate filtered and washed with C6H6. The filtrate is made acidic to Congo red and the 2 layers formed are separated The H2O layer is extracted thrice with C6H6 and the combined C6H6 solutions are washed successively with 2.0 N H2SO4 and Na2CO3 solution, then dried over anhydrous Na2SO4 with a little fused K2CO3. The C6H6 is removed in vacuo and the products (except II) are likewise distilled in vacuo. When IV is used as catalyst CHCl3 (dried over CaCl2) is used as solvent and extractions are made with petr. ether. The following di-tert-Bu esters were prepared: II (87% yield); malonate, b10 93掳 (78% yield); succinate, b14 115掳 (31%); glutarate, b13 125.5掳; adipate, b10 134掳 (60%); pimelate, b11 174掳 (60%); suberate, b11 160掳 (64%); azelate, b13 174掳 (70%); sebacate, b13 185掳 (74%). Several mixed ester-salts were prepared by saponification 1 of the acid radicals with alc. KOH. This study involved multiple reactions and reactants, such as Di-tert-butyl decanedioate (cas: 143050-66-2Name: Di-tert-butyl decanedioate).
Di-tert-butyl decanedioate (cas: 143050-66-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Name: Di-tert-butyl decanedioate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics