O-Alkyl substituted hydroxycarbamates was written by Major, Randolph T.;Dursch, Friedrich;Hess, Hans Jurgen. And the article was included in Journal of Organic Chemistry in 1959.Computed Properties of C9H20O2 The following contents are mentioned in the article:
Some O-alkyl substituted hydroxylamine derivatives possess pharmacol. properties similar to those of related amines. HONHCO2Et (I), the related compound MeONHCSOEt (II) and various 2,2-dialkyl-1,3-propanediol bis(alkoxyalkylcarbamates), RR1C(CHOCONR2OR3)2 (III) were prepared Finely powd. HONH2.HCl(195 g.) and anhydrous K2CO3 (380 g.) stirred in 1500 mL. Et2O with addition of 20 mL. H2O, the cooled (ice bath) mixture stirred 1 h. with gradual addition of 300 g. ClCO2Et (immediate evolution of CO2) and then overnight at room temperature, the filtered solution evaporated in a slight vacuum and the residue distilled through a 15-cm. Vigreux column in vacuo yielded 66% I, b3 113-16°, giving a deep purple color with aqueous FeCl3. ClCH2CO2H (39 g.) slowly neutralized with 17 g. NaOH in 180 mL. ice-cold H2O and the solution added to 0.30 mol aqueous EtOCS2Na, the mixture kept overnight and concentrated to 150 mL. in vacuo on a steam bath, the cooled concentrate treated with 21 g. MeONH2 and the mixture kept overnight, neutralized with AcOH and extracted with Et2O, the dried (Na2SO4) extract evaporated at room temperature and the residual solid (37 g.) recrystallized (petr. ether, b. 30-60°) yielded 66% II, m. 33-6°. Freshly distilled COCl2 (16.0 g.) in 400 mL. dry PhMe slowly added to 220 g. 1,5-dimethyl-2-phenyl-3-pyrazolone and 70 g. Me2C(CH2OH)2 in 50 mL. CHCl3 at – 10 to 0° (ice-NaCl bath) and the mixture stirred overnight at room temperature, filtered from antipyrine-HCl (almost quant. yield) and the salt washed with Et2O, the combined filtrates evaporated in vacuo and the yellow oily residue distilled yielded 2,2-dimethyl-1,3-propanediol bis(chloroformate), RR1C(CH2OCOCl)2 (IV, R = R1 = Me) (V). Similarly were prepared the analogous IV (R, R1, b.p./mm., and % yield given): Me, Me, 122-5°/17, 56; Et, Et (VI), 153-5°/24, 64; Et, Bu, 165-8°/20, 60. MeONHMe (3.0 g.) and 5.0 g. powd. anhydrous K2CO3 stirred in 30 mL. absolute Et2O (ice-cooling) with gradual addition of 5.0 g. V (slow evolution of CO2), and the mixture stirred 24 h. at room temperature, the Et2O evaporated and the residue taken up in 25 mL. H2O, extracted with Et2O and the oily product distilled yielded 86% III (R = R1 = R2 = R3 = Me) (method A). VI (25.7 g.) in 150 mL. absolute Et2O treated dropwise with 30.5 g. MeON HMe with shaking and cooling, the mixture kept overnight at room temperature and filtered from MeONHMe.HCl, the washed (25 mL. H2O) and dried (Na2SO4) filtrate evaporated and the oily residue distilled yielded 60% III (R = R1 = Et, R2 = R3 = Me) (method B). Similarly were prepared the carbamates III (R, R1, R2, R3, method and b.p./mm. given): Me, Me, Me, Me (VII), A, 183-4°/20; Me, Me, H, Me (VIII), A, 194-5°/1.0; Me, Me, Et, Et (IX), B, 136-8°/0.15; Me, Me, H, Et (X), B, 175-80°/0.5; Et, Et, Me, Me (XI), B, 163-5°/0.3; Et, Et, Et, Et, B, 133.8°/0.1; Et, Bu, Me, Me (XII), B, 166-9°/0.3; Et, Bu, Et, Et, B, 142.8°/0.2. None of the compounds I, MeONHCO2Et, EtONHCO2Et (XIII), II, VIII, X, and XII inhibited Sarcoma 180 in vivo at non-toxic doses. XIII showed little effect in mice (i.p. in Mazola oil) in doses below the toxic level of 441 mg./kg. but EtONEtCO2Et (XIV) produced depression at or near the lethal level of 1069 mg./kg. XIV (1% suspension in tragacanth) abolished the corneal reflex 18 min. on instillation into the rabbit eye. VIII-XII were inactive in tests designed to test their activity in mice similar to that produced by meprobamate. This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Computed Properties of C9H20O2).
2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Computed Properties of C9H20O2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts