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Citation: ZHANG Ming-Xiao, LI Xue-Gang. One-pot Synthesis of 5-Hydroxy-1,4-naphthoquinones from Acetic Anhydride,Hydrogen Peroxide and 1,5-Dihydroxy Naphthalene[J]. Chinese Journal of Applied Chemistry, ;2007, 24(12): 1470-1472. shu

One-pot Synthesis of 5-Hydroxy-1,4-naphthoquinones from Acetic Anhydride,Hydrogen Peroxide and 1,5-Dihydroxy Naphthalene

ZHANG Ming-Xiao ^a,c ,
LI Xue-Gang ^b,c,,

1.
a College of Chemistry and Chemical Engineering;
2.
b College of Pharmacy;
3.
c Institute of Pharmaceutical Resources Chemistry, Southwest University, Chongqing 400716

Corresponding author: LI Xue-Gang,
Received Date: 12 January 2007
Available Online: 18 May 2007

5-Hydroxy-1,4-naphthoquinone was synthesized in one pot by dropping methanol solution of 1,5-dihydroxy naphthalene to peroxyacetic acid formed from acetic anhydride and hydrogen peroxide without H₂SO₄ with a yield of 68%.The product was purified by recrystallization from benzene,and its structure was confirmed by HPLC,UV,FTIR,¹H NMR and ¹³C NMR.The reaction conditions,such as the ratio of the reactants,reaction temperature and reaction time,were optimized.The optimum molar ratio was 1:4:8 of 1,5-dihydroxy naphthalene,acetic anhydride and hydrogen peroxide.The reaction temperature was 40~60℃ and the reaction time 5.5 h.The results suggest that the one-pot-method is an efficient and convenient synthesis approach of juglone without using H₂SO₄ and purification of peroxyacetic acid by vacuum distillation.
- Juglone,
- hydroxy-naphthoquinones,
- one-pot-method,
- synthesis
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