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(3-ETHOXY-PHENOXY)-ACETIC ACID synthesis

3synthesis methods
-

Yield:6459-12-7 100%

Reaction Conditions:

with water;potassium hydroxide in ethanol; for 0.75 h;

Steps:



A 1 L flask fitted with a stir-bar was charged with the ethyl ester from above (33.2 g, 148 mmol) and EtOH (400 mL). To the resultant solution was added KOH (16.6 g, 296 mmol) in H2O (60 mL) forming a thick suspension of crystals. The mixture was stirred for 45 min, then 1 M HCI (300 mL) was added to give a solution with a pH of ~1 . The mixture was concentrated in vacuo to -300 mL. The resultant crystals were filtered, pressed with rubber dam, and rinsed with H2O (3 χ 40 mL). The crystals were dried to give 29.0 g of 3-ethoxyphenoxyacetic acid as a white, crystalline solid (100%). 1 H NMR (60 MHz, CDCI3): δ 7.2-6.9 (m, 2H), 6.6-6.3 (m, 2H), 4.6 (s, 2H), 4.0 (qt, 2H), 1 .5 (t, 3H) ppm. HPLC analysis (0:10:90 H2O:A1 :MeOH) showed a purity of greater than 99% with a retention time of 3.3 min.

References:

WO2013/101911,2013,A2 Location in patent:Page/Page column 29