Uses
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is an antioxidant that is used in polyethylene.
Definition
ChEBI: Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester is an alkylbenzene.
Synthesis
(1) 2,6-di-tert-butylphenol (20.6 g), zinc carbonate (mass ratio 1.5) and tributyltin acetate (0.072 g) were added to a three-necked flask fitted with a mechanical stirrer, a nitrogen introduction tube and a dropping funnel under nitrogen atmosphere. The mixture was melted under nitrogen protection and heating conditions to form a reaction system.
(2) When the temperature of the reaction system rose to 70°C, methyl acrylate (8.24 g) was slowly added through a dropping funnel. After the dropwise addition was completed, the reaction was continued with stirring for 0.5 hours. The reaction temperature was then raised to 90 °C and maintained for 1 hour. After completion of the reaction, it was cooled to 80 °C and the reaction solution was adjusted to neutral with dilute hydrochloric acid to induce crystallization of the product. After filtration, methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate was obtained in 99% yield and 99.5% purity without recrystallization.
References
[1] Patent: CN108358781, 2018, A. Location in patent: Paragraph 0046-0049
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 8.2, p. 1677 - 1682
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, # 8, p. 1829 - 1835
