Synthesis
Example 1: Synthesis of ethyl 2,2-dimethylphenylacetate
In a 10L three-necked flask, 2-methyl-2-phenylpropanecarboxylic acid (500g, 3.1 mol) and 2.5L of dichloromethane were added and dissolved with stirring at room temperature. Subsequently, thionyl chloride (750 g, 6.3 mol) was added slowly, and after addition, the reaction system was heated to reflux and maintained for 15 hours. After the reaction was completed, cooled to room temperature, 400mL of anhydrous ethanol was added slowly dropwise, and stirring was continued for 2 hours after the dropwise addition. The reaction solution was adjusted to pH 9-10 with 10% NaOH solution and the completion of the reaction was monitored by thin layer chromatography (TLC). The organic layer was separated, washed twice each with saturated sodium bicarbonate solution and saturated sodium chloride solution in turn, and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give a colorless oily product, ethyl 2,2-dimethylbenzeneacetate 560 g, 96% yield.
References
[1] Patent: CN104276952, 2016, B. Location in patent: Paragraph 0027; 0028
[2] MedChemComm, 2013, vol. 4, # 2, p. 367 - 370
[3] Tetrahedron, 2009, vol. 65, # 2, p. 456 - 460
[4] Journal of the American Chemical Society, 1968, vol. 90, p. 2082 - 2096
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 8, p. 717 - 718
