Some anticonvulsant agents derived from 1,3-propanediols was written by Ludwig, B. J.;Piech, E. C.. And the article was included in Journal of the American Chemical Society in 1951.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol The following contents are mentioned in the article:
Mono- and dicarbamate esters of 2,2-disubstituted-1,3-propanediols were prepared for evaluation as anticonvulsants. Preparation of 2,2-disubstituted-1,3-propanediol dicarbamates. General method: COCl2 (20 g.) in 200 cc. PhMe at -10° treated with a cooled solution of 13.2 g. (HOCH2)2CEt2 and 38 g. antipyrine in 100 cc. CHCl3 (temperature kept at -5 to 0°), the mixture let stand overnight at room temperature, filtered, the filtrate treated with NH3 (moderate cooling), the amide filtered off, extracted with 250 cc. cold water, and recrystallized from water yielded 17.5 g. di-Et compound (I). The PhMe-CHCl3 filtrate concentrated and the residue distilled in vacuo yielded 75% 2,2-diethyl-1,3-propanediol bis(chlorocarbonate), b4.5 108°, nD25 1.4628. For the compounds RR’C(CH2OCONH2)2, R, R’, yield (%), and m.p. (all m.ps. uncorrected) are: Me, Me, 82, 151.5-2.5°; Et, Me, 65, 135-6°; Me, Pr, 90, 105-6°; Me, iso-Pr, 61, 99-100°; Et, Et, 80, 149-50°; Et, Bu, 63, 117-18°; Et, Ph, 70, 119-20°; Pr, Pr, 87, 152-3°; RR’ = (CH2)5, 60, 112-13°. N-Substituted-2,2-diethyl-1,3-propanediol dicarbamates were prepared by the same procedure (R, yield (%), and m.p. given): Me, 56, 85-6°; Ph, 67, 135.5-6.5°; Ac, 65, 123-4°; PhCH2CO2, 20, 204-5°; Et, 50,-[bis(diethylamino) derivative b5 130-2°, nD25 1.4569]. The following method yielded cyclic carbonate derivatives: a cooled 10% solution of 0.1 mole of COCl2 in PhMe added to 13.2 g. I and 0.2 mole antipyrine in a min. of CHCl3 (temperature held at 25°), the mixture held at 25° overnight, filtered, the filtrate concentrated, the residue dissolved in Et2O, the Et2O solution extracted with water, and the Et2O evaporated yielded 10.5 g. 5,5-diethyl-2-m-dioxanone, b2 131-2°, m. 45-6° (from C6H6-petr. ether). For other 5,5-disubstituted-2-m-dioxanones, R, R’, yield (%), and m.p. are: Me, Me, 60, 110-11°; Me, Pr, 74, b0.25 95-104°, nD25 1.4550; Et, Et, 66, 45-6°; Et, Bu, 80, b1 125-30°, nD25 1.4638; Et, Ph, 85, 99.5-100.5°. A 5,5-disubstituted-2-m-dioxanone (5 g.) in a stainless-steel pressure bomb cooled in Dry Ice, 7.5 cc. NH3 added, the vessel closed and shaken 48 hrs. at room temperature, and the NH3 evaporated yielded 2,2-disubstituted-3-hydroxypropyl carbamates, HOCH2CRR’CH2OCONH2 (R, R’, yield (%), and m.p. given): Me, Me, 53, 60-1°; Me, Pr, 60, 61.5-2.5°; Et, Et, 75, 75-6°; (N-Me derivative, nD25 1.4640, b0.5 110-16°; N,N-di-Et derivative, nD25 1.4587, b0.5 104-8°); Et, Bu, 73, 66.5-7.5°; Et, Ph, 69, 89-90°. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Quality Control of 2-Butyl-2-ethylpropane-1,3-diol).
2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Quality Control of 2-Butyl-2-ethylpropane-1,3-diol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts