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529133

Sigma-Aldrich

1-Methoxy-2-naphthoic acid

97%

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About This Item

Fórmula lineal:
CH3OC10H6CO2H
Número de CAS:
883-21-6
Peso molecular:
202.21
MDL number:
MFCD00094169
UNSPSC Code:
12352100
PubChem Substance ID:
24877652
NACRES:
NA.22

assay

97%

mp

125-129 °C (lit.)

SMILES string

COc1c(ccc2ccccc12)C(O)=O

InChI

1S/C12H10O3/c1-15-11-9-5-3-2-4-8(9)6-7-10(11)12(13)14/h2-7H,1H3,(H,13,14)

InChI key

PMJACRPIWSINFF-UHFFFAOYSA-N

General description

1-Methoxy-2-naphthoic acid can be prepared from 1-methoxynaphthalene. 1-Methoxy-2-naphthoic acid can also be synthesized by reacting potassium tert-butoxide with 1-methoxynaphthalene and butyllithium in the presence of cyclohexane and tetrahydrofuran. It undergoes reduction in the presence of lithium to afford tetrahydronaphthoic acid.

Application

1-Methoxy-2-naphthoic acid may be used in the synthesis of 2-(1-methoxy-2-naphthyl)-4,4-dimethyl-2-oxazoline. It may also be used in the synthesis of the following compounds:
  • 1-sec-butyl-2-naphthoic acid
  • 1-tert-butyl-2-naphthoic acid
  • 1-ethyl-2-naphthoic acid
  • 1-vinyl-2-naphthoic acid
  • 1-phenyl-2-naphthoic acid
  • 1-(2,5-dimethylphenyl)-2-naphthoic acid
  • 2′-methoxy-[1,1′-binaphthalene]-2-carboxylic acid

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Eva Castagnetti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(4), 799-804 (2002-02-22)
Judged by its capacity to promote a hydrogen/metal permutation at an ortho position, the trifluoromethoxy group is superior to both the methoxy and trifluoromethyl groups. Moreover, like CF(3) and unlike OCH(3), OCF(3) exerts a long-range effect that still considerably lowers
Chemistry of aryloxazolines. Applications to the synthesis of lignan lactone derivatives.
Meyers AI and Avila WB.
The Journal of Organic Chemistry, 46(19), 3881-3886 (1981)
The metalation of 1-methoxynaphthalene with n-butyllithium.
Graybill BM and Shirley DA.
The Journal of Organic Chemistry, 31(4), 1221-1225 (1966)
Birch Reduction of 2-Naphthoic and of ortho-Methoxynaphthoic Acids.
Eliel EL and Hoover TE.
The Journal of Organic Chemistry, 24(7), 938-942 (1959)
Regadia Aissaoui et al.
The Journal of organic chemistry, 77(1), 718-724 (2011-11-24)
Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need

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