2-(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetic acid synthesis

5synthesis methods

Product Name:2-(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetic acid
CAS Number:27533-69-3
Molecular formula:C13H14O3
Molecular Weight:218.25

Acetic acid, 2-cyano-2-(3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)-, ethyl ester

139157-83-8
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2-(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetic acid

27533-69-3
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Yield:27533-69-3 71.6%

Reaction Conditions:

with sodium hydroxide in ethanol;water at 25 - 30;

Steps:

2-(1,2-Dihydro-6-methoxynaphthalen-4-yl)acetic acid (3)

To a solution of step-1 (mixture of exo andendo) (6 g, 22.1 mmol), in ethanol (60.0 mL, 10 vol) at 25-30 °C, was added 50 % NaOH (8.84 g, 221.1 mmol) solutiondrop wise in to reaction mass at 0-5 °C. After addition, themixture was stirred for overnight at 25-30 °C. Reaction masswas concentrated completely under reduced pressure and obtained crude was purified by column chromatography on100-200 silica gel by eluting 50 % ethyl acetate in n-hexane,to get off-white solid (3.45 g, 71.6 % yield).IR (KBr, νmax, cm-1): 3017, 2927, 2842, 2731, 2642, 2533,2362, 2338, 2082, 1876, 1712, 1492, 1461, 1698, 1566, 1407,1444, 1298, 1373, 1335, 1251, 1220, 1197, 1170, 1080, 1042,392, 889, 812, 754, 731, 656; 1H NMR (400 MHz, CDCl3): δ7.04 (d, J = 8.0 Hz, 1H), 6.80 (d, J = 2.4 Hz, 1H), 6.8 (dd, J1 =2.8 Hz, J2 = 8.0 Hz, 1H), 6.02 (t, J = 4.4 Hz, 1H), 4.14 (q, J =7.1 Hz, 2H), 3.78 (s, 3H), 3.41 (s, 1H), 3.40 (s, 1H), 2.72 (t,J = 8.0 Hz, 2H), 2.23-2.32 (m, 2H), 1.24 (t, J = 7.4 Hz, 3H);EI-MS m/z (272.21 %, M + 1).

References:

Gurunadham;Raju, R. Madhusudhan;Venkateswarlu [Asian Journal of Chemistry,2016,vol. 28,# 6,p. 1367 - 1370]

4521-28-2 Synthesis