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ChemicalBook CAS DataBase List VIOLANTHRONE-79
85652-50-2

VIOLANTHRONE-79 synthesis

2synthesis methods
1-Bromooctane

111-83-1

DIHYDROXYDIBENZANTHRONE

128-59-6

VIOLANTHRONE-79

85652-50-2

General procedure for the synthesis of 16,17-bis(octyloxy)anthraceno[9,1,2-cde]benzo[rst]pentafene-5,10-dione from 1-bromooctane and 16,17-dihydroxyanthraquinone violet: 1.21 g (2.48 mmol) of 16,17-dihydroxyanthraquinone violet was placed in a 100 mL round-bottomed flask, and 50 mL of N-methylpyrrolidone (NMP ), heated to 100 °C and maintained for 10 min to ensure that 16,17-dihydroxyanthrone violet was well dispersed. Subsequently, 1.00 g (7.2 mmol) of anhydrous K2CO3, 0.98 g (5.08 mmol) of 1-bromooctane, and a catalytic amount of 18-crown-6 were added to the reaction system. the reaction was maintained at 100 °C, and the reaction was terminated with continuous stirring for 8 h. The reaction temperature was maintained at 100 °C, and the reaction temperature was maintained at 100 °C for 10 min. The reaction mixture was slowly poured into 100 mL of water, stirred thoroughly and filtered, the solid was collected and dried to obtain the crude product. The crude product was dissolved with dichloromethane and filtered to remove insoluble material. The dichloromethane was removed by rotary evaporator to obtain the solid product, which was weighed after drying as 1.26 g with 72% yield. Finally, the product was further purified by silica gel column chromatography using a solvent mixture of dichloromethane and methanol at a volume ratio of 20:1 as eluent.

-

Yield: 72%

Reaction Conditions:

with 18-crown-6 ether;potassium carbonate in 1-methyl-pyrrolidin-2-one at 100; for 8 h;Williamson Ether Synthesis;

Steps:

3 Implementing example three , 16, 17- two Xin Yangji Anthracyclinone purple preparation
Taking 1.21g (2.48mmol) 16, 17-dihydroxy Anthracyclinone purple puts in 100 ml flask, add 50mLN-methyl pyrrolidone, heating 10 min to 100 °C the 16, 17-dihydroxy Anthracyclinone purple disperse as much as possible. Then add 1.00g (7.2mmol) no water K2CO3, 0.98g (5.08mmol) 1-polybromide octane, and presence of 18-crown -6. Maintain reaction temperature 100 °C, reaction 8 hours the reaction is stopped.The reaction solution is poured into 100 ml water, fully mixing, filtering, drying to obtain the crude product. Dichloromethane is used for dissolving the crude product, filtering to remove undissolved components. turns on lathe does dichloromethane, to obtain the solid, dried to obtain 1.26g grams of product, yield is 72%. The silica gel chromatographic column, to CH2Cl2: CH3OH=20 1 as eluant, further elution separation and purification.

References:

Beijing University of Chemical Technology;Zhuang, Junpeng;Liu, Jie;Hao, Haijun;Niu, Junyu CN103804163, 2016, B Location in patent:Paragraph 0036; 0037; 0038

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