Synthesis
Step 24b: 2-(4-Methoxyphenyl)-2-methylpropionitrile (Compound 0802-27, 1.63 g, 9.30 mmol) was dissolved in ethylene glycol (3.40 mL) followed by addition of potassium hydroxide (1.29 g, 22.99 mmol) and water (0.46 mL). The reaction mixture was heated and stirred at 150 °C for 7 hours. Upon completion of the reaction, the mixture was poured into water and the pH was adjusted with concentrated hydrochloric acid to 2. The reaction mixture was filtered, the collected solid was washed with water and dried under vacuum to afford the target product 2-(4-methoxyphenyl)-2-methylpropanoic acid (Compound 0803-27, 0.85 g, 47% yield) as a white solid. The product was analyzed by LCMS showing [M+1]+ of 195. 1H NMR (DMSO-d6) data were as follows: δ 1.44 (s, 6H), 3.73 (s, 3H), 6.88 (d, J=9.2 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 12.23 (s, 1H).
References
[1] European Journal of Organic Chemistry, 2007, # 21, p. 3449 - 3462
[2] Patent: WO2009/36016, 2009, A1. Location in patent: Page/Page column 77; 78
[3] Acta Chemica Scandinavica (1947-1973), 1954, vol. 8, p. 1203,1207
[4] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 210,214
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 4801,4805
