Helberger, Johann Heinrich’s team published research in Justus Liebigs Annalen der Chemie in 586 | CAS: 183278-30-0

Justus Liebigs Annalen der Chemie published new progress about 183278-30-0. 183278-30-0 belongs to ethers-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain,Ether, name is Sodium 4,4′-oxybis(butane-1-sulfonate), and the molecular formula is C8H16Na2O7S2, Related Products of ethers-buliding-blocks.

Helberger, Johann Heinrich published the artcileOrganic sulfonic acids. V. Syntheses of 1,4-butanesultone, Related Products of ethers-buliding-blocks, the publication is Justus Liebigs Annalen der Chemie (1954), 158-64, database is CAplus.

To 216 g. O.CH2.CH2.CH2.CH2 and 1.5 Zn dust was added slowly 237 g. AcCl; the mixture warmed initially at 40°, later at 60°, allowed to stand overnight, and heated 4 hrs. at 100°, giving 330 g. AcO(CH2)3CH2Cl, b15 85°, 300 g. of which, refluxed 28 hrs. under N with 262 g. Na2SO3 in 1 l. H2O, followed by concentration in vacuo, addition of 0.51. concentrated HCl, saturation with HCl gas, addition of MeOH, filtration, and concentration gave 280 g. HOCH2(CH2)3SO3H. Heating this acid 1.5 hrs. at 120-30°/16 mm., distilling, and removing dissolved SO2 by N yielded 221 g. CH2.(CH2)3.SO2.O (I), b13 149-50°, large plates, m. 14.5°, nearly insoluble in cold. H2O and CCl4 soluble in Et2O, CHCl3, C6H6, and EtOH, hydrolyzed quantitatively to the sulfonic acid by boiling 1.5 hrs. with H2O. [Cl(CH2)4]2O (198 g.) heated and stirred under N 58 hrs. with 264 g. Na2SO3 in 1 l. H2O, filtered, treated with BaCl2, refiltered, and evaporated to dryness in vacuo gave [NaO3SCH2(CH2)3]2O, which with saturated HCl and MeOH gave 92.3% of the corresponding free acid (II), uncrystallizable sirup. The Na salt of II, with PCl5 and CCl4 gave 78% acid chloride, oil, which, in Et2O at -50° with liquid NH3, formed [H2NO2S(CH2)4]2O, needles, m. 104.5° (from H2O). II (76 g.), heated 10 hrs. at 120-5°/6 mm., gave 66.8 g. I, b5 135-6°. As in previous publications, I gave the following hygroscopic sulfobetaines in excellent yields: (from pyridine) C9H13O3NS, m. 249-50° (decomposition); (from PhNMe2) C12H19O3NS, m. 272-3° (decomposition); (from PhNH2, noncrystalline glass. EtOH (15 cc.) saturated with NH3 at 0° and heated with 1.36 g. I at 60-5° gave 1.45 g. H2N(CH2)4SO3H, m. 222-3° (decomposition) (from MeOH). The following crystalline adducts of I were also formed in 92-96% yields, by heating I with the appropriate salts or phenolates in suitable solvents: NC(CH2)4SO3K, SN C(CH2)4SO3K, I(CH2)4SO3K, PhOCH2(CH2)3SO2Na, PhSCH2(CH2)3SO3Na, and (from K phthalimide). o-C6H4(CO)2N(CH2)4SO3K.

Justus Liebigs Annalen der Chemie published new progress about 183278-30-0. 183278-30-0 belongs to ethers-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain,Ether, name is Sodium 4,4′-oxybis(butane-1-sulfonate), and the molecular formula is C8H16Na2O7S2, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem