ChemicalBook CAS DataBase List 2,3-dihydroxyterephthalic acid

2,3-dihydroxyterephthalic acid synthesis

6synthesis methods

Product Name:2,3-dihydroxyterephthalic acid
CAS Number:19829-72-2
Molecular formula:C8H6O6
Molecular Weight:198.13

124-38-9
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120-80-9 Synthesis

120-80-9
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19829-72-2
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Yield:19829-72-2 95%

Reaction Conditions:

Stage #1: carbon dioxide;benzene-1,2-diolwith potassium carbonate at 230 - 250; under 19652.1 - 60507.9 Torr; for 19.25 h;
Stage #2: with hydrogenchloride in lithium hydroxide monohydrate; for 5 h;

Steps:

1 2,3-dihydroxyterephthalic acid (1)

2,3-dihydroxyterephthalic acid (1)
On a warm, sunny day (28° C., 18% humidity), catechol (TCI, 120.033 g, 1.09 mol) and K₂CO₃(316 g, 2.29 mol) were ground together, and the homogeneous mixture was poured into a 500-mL beaker, which was placed in a par-bomb. The bomb was purged three times with 600 psi CO₂before being filled to 860 psi CO₂and placed in an oil bath. The oil bath gradually increased in temperature to 225° C. in 3 h, with an accompanying increase in bomb pressure to 1170 psi. Within 1.25 h, the pressure decreased to 380 psi (250° C.), and the temperature was maintained at 230° C. for 15 hours. The bomb, at 160 psi, was let cool to RT (and placed in the freezer to facilitate opening) and opened. The reaction mixture, a hard gray rock with turquoise and white specks, was combined with 1.5 L water and 1 L conc. HCl. The mixture slowly bubbled and produced beige foam, and after 3 h, the solid chunks were broken apart with a stick and stirred with a magnetic stir bar for 2 h. The beige slurry was then filtered and left to dry on the house vacuum for 14 h. The solid light gray solid was washed with 4 L Millipore water, and left on the house vacuum for 9 days. The dried gray solid was ground to a powder and further dried on the vacuum line for 26 h (95%).
¹H NMR (400 MHz, MeOD, δ): 7.34 (s, Ar H, 2H).
¹³C NMR (101 MHz, MeOD, δ): 117.8, 120.1, 152.6, 173.2.
HRMS-ESI (m/z): [M-H]^- calcd for C₈H_SO₆, 197.0092. found, 197.0094.