ChemicalBook CAS DataBase List 3-(6-methoxynaphthalen-2-yl)propanoic acid

3-(6-methoxynaphthalen-2-yl)propanoic acid synthesis

10synthesis methods

Product Name:3-(6-methoxynaphthalen-2-yl)propanoic acid
CAS Number:3453-40-5
Molecular formula:C14H14O3
Molecular Weight:230.26

2-Naphthalenepropanoic acid, 6-methoxy-, methyl ester

136579-95-8
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3-(6-methoxynaphthalen-2-yl)propanoic acid

3453-40-5
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Yield:3453-40-5 97%

Reaction Conditions:

with water;sodium hydroxide in tetrahydrofuran;methanol at 20; for 2 h;

Steps:

10 Preparation of Compound 66

To a solution of methyl ester 64 (46.5 g, 191 mmol) in THF/MeOH/H₂O (500 mL/500 mL/150 mL) was added NaOH (45.6 g, 114 mmol) and the reaction mixture was stirred at room temperature for 2 h. Solvent was removed and pH value was adjusted to 1 with 1 N aq HCl; white solid precipitated out. Solid was filtered, washed with water and dried under vacuum to afford acid 66 (42.5 g, 97%) as a white solid: ¹H NMR (400 MHz, DMSO-d₆) δ 12.14 (brs, 1H), 7.73 (dd, J=9.5, 2.3 Hz, 2H), 7.64-7.61 (m, 1H), 7.35 (dd, J=8.5, 1.5 Hz, 1H), 7.26 (d, J=2.8 Hz, 1H), 7.12 9 (dd, J=9.1, 2.5 Hz, 1H), 3.85 (s, 3H), 2.94 (t, J=7.6 Hz, 2H), 2.60 (t, J=7.6 Hz, 2H).

References:

US2014/171447,2014,A1 Location in patent:Paragraph 0321; 0325