Preparation
synthesis of methyl phenoxyacetate: methyl bromoacetate (10 mL, 105.6 mmol) and phenol (9.9380 g, 105.6 mmol) were dissolved in 250 mL of acetone; K2CO3 (21.89 g, 158 mmol) and KI (5 g, 30 mmol) were added and the mixture heated to reflux with stirring overnight. The mixture was filtered and the resultant solution concentrated in vacuo. Deionized water (200 mL) was added. The reaction mixture was extracted with 50 mL ethyl acetate three times. The combined ethyl acetate layers were washed with brine, dried over MgSO4, and filtered. All ethyl acetate was removed in vacuo, resulting in a slightly yellow liquid (80% yield).
Synthesis
9.4 g of phenol was dissolved in 100 μL of N,N-dimethylformamide and 11.9 g of methyl chloroacetate and 20.7 g of potassium carbonate were added sequentially. The reaction mixture was heated to 50 °C and stirred continuously for 12 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 300 mL of ice water was added to the reaction system. The aqueous phase was extracted twice with 200 mL of ethyl acetate and the organic phases were combined. The organic phase was sequentially washed three times with 400 mL of saturated sodium chloride solution and dried over anhydrous sodium sulfate. After the solvent was removed by concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent ratio of petroleum ether:ethyl acetate=20:1) to afford 15.2 g of a light yellow oily product, methyl phenoxyacetate, in 92.0% yield.
References
[1] Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 6, p. 1317 - 1332
[2] Synthetic Communications, 2005, vol. 35, # 13, p. 1759 - 1764
[3] Patent: CN108570028, 2018, A. Location in patent: Paragraph 0017-0018
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 1, p. 132 - 140
[5] Asian Journal of Chemistry, 2013, vol. 25, # 11, p. 6189 - 6191
