ChemicalBook CAS DataBase List 6-METHOXY-1-NAPHTHOIC ACID

6-METHOXY-1-NAPHTHOIC ACID synthesis

13synthesis methods

Product Name:6-METHOXY-1-NAPHTHOIC ACID
CAS Number:36112-61-5
Molecular formula:C12H10O3
Molecular Weight:202.21

Methyl 6-Methoxynaphthalene-1-carboxylate

61109-48-6
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36112-61-5
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Yield:36112-61-5 95%

Reaction Conditions:

with potassium hydroxide in tetrahydrofuran;water at 100; for 4 h;

Steps:

5.2.15. 6-methoxy-1-naphthoic acid (9a)

Method D: to a solution of compound 8a (1.70 g, 7.87 mmol) inTHF (6 mL) was added a 85% aqueous potassium hydroxide solution(3 mL). The mixture was stirred at 100 C for 4 h, cooled to roomtemperature, and acidified with a 1 M HCl solution. The resultingprecipitate was filtered and washed with water to afford thedesired acid 9a (1.51 g, 95%) as a-pink solid.Mp 95.3 C. 1H NMR (300 MHz, DMSO-d6) d 8.77 (d, 1H,J 9.3 Hz, H8), 8.04 (dd, 1H, J 8.1, 1.2 Hz, H2), 7.97 (dd, 1H, J 8.4,1.2 Hz, H4), 7.53 (dd, 1H, J 8.4, 8.1 Hz, H3), 7.42 (d, 1H, J 2.7 Hz,H5), 7.28 (dd, 1H, J 9.3, 2.7 Hz, H7), 3.89 (s, 3H, CH3). 13C NMR(75 MHz, DMSO-d6) d 168.8, 157.1, 135.2, 131.9, 127.7, 127.5, 127.2,126.1, 125.5, 120.0, 106.7, 55.3.

References:

Moine, Espérance;Dimier-Poisson, Isabelle;Enguehard-Gueiffier, Cécile;Logé, Cédric;Pénichon, Mélanie;Moiré, Nathalie;Delehouzé, Claire;Foll-Josselin, Beátrice;Ruchaud, Sandrine;Bach, Stéphane;Gueiffier, Alain;Debierre-Grockiego, Fran?oise;Denevault-Sabourin, Caroline [European Journal of Medicinal Chemistry,2015,vol. 105,p. 80 - 105]

201230-82-2 Synthesis