Synthesis
The general procedure for the synthesis of (R)-2-(benzyloxy)propionic acid from methyl (R)-2-(benzyloxy)propionate was as follows: potassium hydroxide (KOH, 9.2 g, 163.96 mmol, 3.00 eq.) was added to methyl (2R)-2-(benzyloxy)propionate (11 g, 56.63 mmol, 1.00 eq.) in a methanol/water (90 mL/10 mL) solution. The reaction mixture was stirred at room temperature for 30 minutes. Upon completion of the reaction, the reaction mixture was concentrated and subsequently diluted with water. The resulting aqueous solution was washed with ethyl acetate and the pH of the aqueous layer was adjusted with aqueous hydrochloric acid to 5. The acidified aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum to give 9.6 g (94% yield) of (2R)-2-(benzyloxy)propionic acid as a colorless oil.LC-MS detection showed [M + H]+ = 179.
References
[1] Patent: WO2015/138934, 2015, A1. Location in patent: Paragraph 00174
[2] Tetrahedron Letters, 1998, vol. 39, # 8, p. 779 - 782
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9370 - 9379
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 16, p. 4919 - 4922
[5] Angew. Chem., 2015, vol. 127, # 16, p. 5001 - 5004,4
