Alizarin synthesis

12synthesis methods

Product Name:Alizarin
CAS Number:72-48-0
Molecular formula:C14H8O4
Molecular Weight:240.21

(a) 2 – Bromoanthraquinone and Potassium hydroxide heating; (b) 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid (Sodium) and Sodium hydroxide and Sodium nitrate and Sodium chlorate heating; (C) Anthracene-9,10-dione?and Sodium hydroxide and Sodium chlorate and Sodium nitrate heating (GP 186526); (d) in the presence of Sodium nitrite and Sodium hydroxide and Anthracene-9,10-dione?and Sodium nitrate heating (GP 241806245 987); (e) in the Oxidant and Sodium sulfite and the presence of lime, anthracene in a nitrocellulose derivatives and Sodium hydroxide heating (GP 292247); (f) 2 – Anthraquinonesulfonic acid in the presence of air, with the Sodium hydroxide Etanol wetting treatment (GP 287270); (g) 2-Chloroanthracene-9,10-dione Sodium chlorate in the presence of alkali fusion for (USP 1744815); (h) 2-Methylanthracene-9,10-dione in the presence of Oxidant, with Sodium hydroxide treatment (BP 293328).

85-44-9 Synthesis

85-44-9
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120-80-9 Synthesis

120-80-9
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72-48-0
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$16.80/25G

Yield:72-48-0 55%

Reaction Conditions:

Stage #1:phthalic anhydride;benzene-1,2-diol with aluminum (III) chloride;sodium chloride at 110 - 165; for 4 h;Friedel Crafts Acylation;
Stage #2: with hydrogenchloride in water at 0 - 100; for 0.75 h;Heating / reflux;

Steps:

A mixture of anhydrous AlCl₃(5 mmol, 0.667 g) and pre-baked NaCl (2.5 mmol, 0.145 g) was heated (110° C.) in an oil bath till molten. A homogenous mixture of phthalic anhydrides, (1 mmol) and substituted phenols, (1 mmol) were reacted with AlCl₃/NaCl melt. The temperature was slowly increased and maintained at 165° C. for 4 h. The reaction mixture was cooled to 0° C., 10 ml of 10% HCl added, stirred for 15 min at 0° C. and refluxed at 100° C. for 30 min. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The resulting product was purified by C₁₈MPLC column using acetonitrile:water (1:1) as the mobile phase.; UV λ_max(CH₃OH) (log ε): 205 (4.47), 246 (4.6), 275 (4.4), 431 (3.7). ¹H NMR (DMSO): δ 7.27 (d, 1H, J=8.5), 7.70 (d, 1H, J=8.5), 7.95 (m, 2H), 8.23 (m, 2H). ¹³C NMR (DMSO): 190.25, 182.03, 154.2, 152.28, 136.57, 135.51, 135.04, 134.16, 128.59, 127.95, 125.26, 122.70, 122.31, 117.73. Yield: 55%.

References:

Board of Trustees of Michigan State University US2005/267307, 2005, A1 Location in patent:Page/Page column 4, 5

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120-80-9 Synthesis

120-80-9
539 suppliers
$13.00/25g