Synthesis
The general procedure for the synthesis of methyl 3-hydroxy-4-iodobenzoate from methanol and 3-hydroxy-4-iodobenzoic acid was as follows: first, 61.31 g of 3-hydroxy-4-iodobenzoic acid was obtained, which presented as a white solid. Subsequently, 47 g (150 mmol) of 3-hydroxy-4-iodobenzoic acid was dissolved in 300 mL of methanol and 6.13 g (35.6 mmol) of p-toluenesulfonic acid was added as a catalyst. The reaction mixture was heated continuously at 70 °C for 48 hours. Upon completion of the reaction, the reaction was terminated by adding 11 μL of water. The precipitated product was filtered and washed with distilled water to neutral pH. finally, 37.4 g (76% yield) of methyl 3-hydroxy-4-iodobenzoate was obtained as a beige powder.
References
[1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 83, p. 10328 - 10330,3
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 9, p. 1103 - 1114
[3] Patent: US2009/12129, 2009, A1. Location in patent: Page/Page column 21
[4] Patent: US2003/232853, 2003, A1. Location in patent: Page 38
[5] Patent: WO2006/18325, 2006, A1. Location in patent: Page/Page column 26
