Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst
Publication type: Journal Article
Publication date: 2009-05-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A new strategy to 6-hydroxy-2-naphthoic acid (HNPA) and 4-hydroxybenzoic acid from 2,6-diisopropylnaphthalene and p -cymene, respectively, was developed using the NHPI-catalyzed aerobic oxidation as a principal reaction. 2,6-Diisopropylnaphthalene was oxidized by the oxidation with O 2 (1 atm) by NHPI (10 mol %) combined with Co(OAc) 2 (0.5 mol %) to give 6-acetyl-2-isopropylnaphthalene, which then was converted to 6-isopropyl-2-naphthoic acid under O 2 (1 atm) in the presence of Co(OAc) 2 (0.5 mol %) and Mn(OAc) 2 (0.5 mol %). Esterification of the resulting acid followed by the aerobic oxidation produced methyl 6-hydroxy-2-naphthoate whose hydrolysis led to the desired HNPA. An alternative route involves the oxidation of 6-acetyl-2-isopropylnaphthalene to 6-acetyl-2-naphthol on which subsequent oxidation and deacetylation gave HNPA. This method was successfully extended to the synthesis of 4-hydroxybenzoic acid from p -cymene.
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Nakamura R., Obora Y., Ishii Y. Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst // Tetrahedron. 2009. Vol. 65. No. 18. pp. 3577-3581.
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Nakamura R., Obora Y., Ishii Y. Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst // Tetrahedron. 2009. Vol. 65. No. 18. pp. 3577-3581.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2009.03.013
UR - https://doi.org/10.1016/j.tet.2009.03.013
TI - Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst
T2 - Tetrahedron
AU - Nakamura, Ryota
AU - Obora, Yasushi
AU - Ishii, Yasutaka
PY - 2009
DA - 2009/05/01
PB - Elsevier
SP - 3577-3581
IS - 18
VL - 65
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2009_Nakamura,
author = {Ryota Nakamura and Yasushi Obora and Yasutaka Ishii},
title = {Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst},
journal = {Tetrahedron},
year = {2009},
volume = {65},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/j.tet.2009.03.013},
number = {18},
pages = {3577--3581},
doi = {10.1016/j.tet.2009.03.013}
}
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MLA
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Nakamura, Ryota, et al. “Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst.” Tetrahedron, vol. 65, no. 18, May. 2009, pp. 3577-3581. https://doi.org/10.1016/j.tet.2009.03.013.