15/05/2022 21:50 One-pot Synthesis of 2-Hydroxy-1,4-Naphthoquinone (Lawsone) | Bentham Science

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Current Organic Synthesis Research Article

Editor-in-Chief
One-pot Synthesis of 2-Hydroxy-1,4-
Naphthoquinone (Lawsone)
ISSN (Print): 1570-1794

Author(s):
Dhanavel Sivakumar, Jayaraman Thanusu, Vijayakumar Kanagarajan,
ISSN (Online): 1875-6271
Samuthira Nagarajan, Haridoss Manikandan and Mannathusamy Gopalakrishnan*
Volume 16 , Issue 3 , 2019
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Subscribe Page: [431 - 434] Pages: 4 Purchase

DOI: 10.2174/1570179416666190111155328 PDF

Price: $65

Abstract
Article
PRC
Metrics
Aims and Scope: The 2-hydroxy-1,4-naphthoquinone (lawsone) and 2,5-dihydroxy-1,
4-
naphthoquninone (5-hydroxylawsone) are synthesized by one step process. The process
50 4 1
involves an
inexpensive catalyst urea hydrogen peroxide and a base (t-BuOK) in alcohol for the
transformation of
1-naphthol or 2,5-dihydroxynaphthalene to lawsone or its derivatives in the
presences of oxygen. The process
is further directed to produce lawsone or its derivatives, with
no extraneous heating to make it energetically efficient.
The synthesized compounds are
2
analyzed by FT-IR, 1H and 13C NMR spectral studies.

Materials and Methods: All the raw materials were purchased from commercial suppliers and 2
Total citations
2
Recent citations
used as such
without further purification. The infrared spectra were recorded on a Thermo
Nicolet-Avatar-330 FT-IR
spectrophotometer using KBr (pellets) and noteworthy absorption 0.36
Field Citation Ratio
values (cm-1) are obtained. 1H and 13C NMR
spectra are recorded at 293K on BRUKER AMX- n/a
Relative Citation Ratio
400 Spectrometer operating with the frequencies of 300
MHz and 75, 125 MHz respectively
using DMSO-d6 as solvent.

Results: The 2-hydroxy-1,4-naphthoquinone (lawsone) and 2,5-dihydroxy-1,4-naphthoquninone

(5-
hydroxylawsone) are synthesised from 1-naphthol and 1,5-dihydorxynaphalene with urea-
hydrogen peroxide as
the catalyst in basic medium and oxygen as the oxidizing agent. After
purification, the formed products are
analysed by IR and NMR spectroscopy. The yield is 82%
and the purity of the products is > 95%. Journal Information

Conclusion: The present study highlights the process for the manufacturing of lawsone and its
About Journal
derivatives
which is efficient in terms of energy needed for the activation of products from
reactants. The advantages
include its cost-effective nature in terms of simple inexpensive
catalyst required for the process and high yield.
The mild reaction conditions employed and the Editorial Board
harmless by product obtained further confirm the usefulness of
this synthetic process.

Keywords: 2-Hydroxy-1, 4-naphthoquinone, Lawsone, green synthesis, spectral analysis, cost- Journal Insight
effective, one-pot synthesis.
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