Chemical Properties
It is white powdery crystal, m.p. 70～72℃, insoluble in water, soluble in benzene, toluene, acetone.
Uses
Methyl 2-(2-Hydroxyphenyl)acetate is used as a reactant in the preparation of caffeic acid phenylethyl esters as antiproliferative agents.
Definition
ChEBI: Methyl (2-hydroxyphenyl)acetate is a member of phenols.
Synthesis
Preparative Example 1A: Synthesis of methyl 2-hydroxyphenylacetate: o-hydroxyphenylacetic acid (400 g, 2.63 mmol) was dissolved in methanol (3.0 L), and the esterification reaction was carried out by passing hydrogen chloride gas into the solution. The reaction was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the reaction mixture was concentrated and dried under vacuum to afford the title compound 1A (415 g, 95% yield), the product was initially a yellow oil and solidified to a solid after standing overnight. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 7.20-7.16 (m, 1H), 7.11-7.09 (m, 1H), 6.93-6.86 (m, 2H), 4.48 (br s, 1H), 3.74 (s, 2H), 3.69 (s, 3H).
References
[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 31, p. 5147 - 5155
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8948 - 8952
[3] Organic Letters, 2008, vol. 10, # 18, p. 3969 - 3972
[4] Patent: WO2015/102990, 2015, A1. Location in patent: Paragraph 0193-0195
[5] Journal of Organic Chemistry, 1994, vol. 59, # 1, p. 203 - 213
