2-(2-Methoxyphenyl)-2-oxoacetic acid synthesis

7synthesis methods

Product Name:2-(2-Methoxyphenyl)-2-oxoacetic acid
CAS Number:26767-06-6
Molecular formula:C9H8O4
Molecular Weight:180.16

66644-69-7 Synthesis

66644-69-7
21 suppliers
$251.00/1g

26767-06-6
8 suppliers
inquiry

Yield:26767-06-6 65%

Reaction Conditions:

with sodium hydroxide in water; for 1.5 h;Heating;

Steps:

Preparation of 2-(2-methoxyphenyl)-2-oxoacetic acid 11

A solution of the ester 10 (17.0 g, 81.7 mmol) and NaOH (12 g, 300 mmol) in water (200 mL) was heating on a steam bath for 1.5 h. Then the solution was washed with diethyl ether, which was discarded,and acidified with dilute HCl leading to precipitation of a yellow oil. The mixture was extracted with diethyl ether again, and the combined ether extracts were dried with MgSO4 and evaporated to give the product (9.5 g, 65%) as deep yellow crystals; mp 96-100°C (lit.,16 102-103 °C); ¹H NMR δ 10.49 (br s,1H, OH), 7.89 (dd, J = 7.8, 1.8 Hz, 1H, H-6), 7.62 (ddd, J = 8.7, 8.4, 1.8 Hz, 1H, H-4), 7.07 (ddd, J = 8.4,7.8, 0.9 Hz, 1H, H-5), 7.02 (dd, J = 8.7, 0.9 Hz, 1H, H-3), 3.90 (s, 3H, OMe); ¹³C NMR δ 185.7 (4ry,CO-Ar), 169.3 (4ry, CO-OH), 160.5 (4ry, C-2), 136.8 (C-4), 130.7 (C-6), 122.0 (4ry, C-1), 121.4 (C-5),112.2 (C-3), 56.0 (OMe). NMR spectra in agreement with lit.29

References:

Aitken, R. Alan;Chang, Da [Heterocycles,2016,vol. 93,# 1,p. 164 - 184]

579-74-8 Synthesis