Sulfuric Acid → 1,2,3,4-Benzenetetrol

Temperatur

4 °C

A solution of myo-2-inosose (11.0 g, 61.2 mmol) in 310 mL of degassed 0.5 M H2SO4 was refluxed under Ar. After 9 h, the solution was cooled to 4° C. and then adjusted to pH 4 by addition of saturated aqueous NaHCO3. Concentration of the reaction solution to 100 mL was followed by continuous liquid-liquid extraction for 18 h using t-butyl methyl ether (500 mL). Upon concentration of the organic layer to 100 mL, a precipitate formed which was filtered, washed with cold hexanes, and dried to afford 1 (4.72 g, 54%) as a tan powder. Addition of hexanes (300 mL) to the filtrate followed by filtering, washing, and drying of the resulting precipitate afforded additional 1 (1.08 g, 12%). mp 162-164° C. 1H NMR (d6-acetone): δ7.24 (s, 4 H), 6.20 (s, 2 H). 13C NMR (d6-acetone): δ139.7, 134.7, 106.2. Anal. Calcd for C6H6O4: C, 50.71; H, 4.23. Found: C, 50.63; H, 4.32. HRMS (FAB) calcd for C6H6O4 (M+H+): 142.0266. Found: 142.0268.

1. extractionConcentration of the reaction solution to 100 mL was followed by continuous liquid-liquid extraction for 18 h
2. customUpon concentration of the organic layer to 100 mL, a precipitate formed which
3. filtrationwas filtered
4. washwashed with cold hexanes
5. customdried

ORD-Eintrag

ord-faabadb17570421f869108a449f99e39

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06750049B1