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ChemicalBook CAS DataBase List Methyl 2-(4-chlorophenyl)-2-methylpropanoate
57225-86-2

Methyl 2-(4-chlorophenyl)-2-methylpropanoate synthesis

5synthesis methods
-

Yield:57225-86-2 89%

Reaction Conditions:

Stage #1: (4-chloro-phenyl)-acetic acid methyl esterwith sodium hydride in N,N-dimethyl-formamide at 0 - 5; for 0.5 h;Inert atmosphere;
Stage #2: methyl iodide in N,N-dimethyl-formamide at 20; for 15.5 h;Inert atmosphere;

Steps:

Methyl 2-(4-chlorophenyl)-2-methylpropanoate (16) [5]

Methyl 2-(4-chlorophenyl)acetate (15; 1.85 g, 10 mmol) was added to a stirredsuspension of NaH (60%, 0.88 g, 22 mmol) in DMF (20 mL) at 0 - 5 °C under an Aratmosphere, followed by being stirred at the same temperature for 0.5 h. MeI (2.5mL, 40 mmol) was added to the mixture, followed by being stirred at the sametemperature for 0.5 h. The mixture stirred at the room temperature for 15 h. The mixture wasquenched with water and extracted twice with AcOEt . The combined organic phase was washedwith water, brine, dried (Na2SO4) and concentrated. The obtained crude oil was purified bySiO2-column chromatography (hexane/AcOEt = 50:1) to give the desired product 16 (1.89 g, 89%).Pale yellow oil;

References:

Taniguchi, Takashi;Taketomo, Yasuaki;Moriyama, Mizuki;Matsuo, Noritada;Tanabe, Yoo [Molecules,2019,vol. 24,# 6,art. no. 1023] Location in patent:supporting information