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ChemicalBook CAS DataBase List 3-Hydroxy-1,8-naphthalic anhydride
23204-36-6

3-Hydroxy-1,8-naphthalic anhydride synthesis

4synthesis methods
5-AMINO-BENZO[DE]ISOCHROMENE-1,3-DIONE

23204-38-8

3-Hydroxy-1,8-naphthalic anhydride

23204-36-6

General procedure for the synthesis of 5-hydroxybenzo[de]isochroman-1,3-dione from 5-amino-1H,3H-benzo[DE]isochroman-1,3-dione: Compound 3 (8 mmol, 1.7 g) was placed in a three-necked flask, and 432 mL of aqueous sulfuric acid solution (sulfuric acid to water in a ratio of 1:5, by volume) was added and the reaction system was cooled down to 0 °C. Subsequently, sodium nitrite (12 mmol, 0.81 g) was slowly added and stirred continuously at 0 °C for 1 hour. After completion of the reaction, the reaction system was gradually warmed to room temperature and then stirred at 120 °C for 12 hours. At the end of the reaction, the reaction mixture was cooled to room temperature, filtered through a Kiriyama funnel and the filter cake was washed with water and dried. The crude product was recrystallized with chloroform to afford the target product 5-hydroxybenzo[de]isochromene-1,3-dione.

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Yield: 90%

Reaction Conditions:

with sulfuric acid;sodium nitrite in water at 0 - 120; for 13 h;

Steps:

(Synthesis of Compound 5 as a Material)
Compound 3 (8 mmol, 1.7 g) was placed in a three-necked flask, 432 mL of an aqueous sulfuric acid solution (sulfuric acid: water 1: 5) was added and the temperature was adjusted to 0 ° C. Sodium nitrite (12 mmol, 0.81 g) was then added and stirred for 1 hour. The temperature was returned to room temperature, and the mixture was stirred at 120 ° C. for 12 hours. After completion of the reaction, the temperature was returned to room temperature, filtered with Kiriyama, washed with water and dried. The crude product was recrystallized from chloroform to obtain the desired product 5.

References:

KYOEISHA CHEMICAL COMPANY LIMITED;KAMEI, TOSHIYUKI;TAKAMATSU, YOSHINORI;TAKENAKA, NAOMI JP2018/39777, 2018, A Location in patent:Paragraph 0115; 0119; 0120

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