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0 °C

2-Methyl-2-phenoxypropionic acid 6 was prepared following the procedure of Corey et al., J. Am. Chem. Soc. 1969;91 :4782. To an ice-cold, stirred suspension of powdered NaOH (3.2 g, 80 mmol) in acetone (40 mL) was added phenol (1.88 g, 20 mmol) followed by 1,1,1-trichloro-2-methyl-2-propanol hydrate (7.82 g, 40 mmol). The mixture was stirred at 0° C. for 2 hours and then at room temperature for 2 hours. The mixture was diluted with H2O, acidified with 2N HCl, and extracted with EtOAc. The organic layer was washed with 2 N HCl, then extracted with saturated NaHCO3 (2×). The aqueous extracts were combined, washed once with EtOAc, acidified with 2N HCl, then extracted with EtOAc (2×). The combined organic layers were washed once with saturated NaCl, dried (MgSO4), and concentrated under reduced pressure. Purification by flash chromatography gave 6 (1.36 g, 38%): 1H NMR (300 MHz, CDCl3) δ 7.28 (t, J=8 Hz, 2H), 7.08 (t, J=8 Hz, 1H), 6.96 (d, J=8 Hz, 2H), 1.52 (s, 6H).

1. custom2-Methyl-2-phenoxypropionic acid 6 was prepared
2. waitat room temperature for 2 hours
3. extractionextracted with EtOAc
4. washThe organic layer was washed with 2 N HCl
5. extractionextracted with saturated NaHCO3 (2×)
6. washwashed once with EtOAc
7. extractionextracted with EtOAc (2×)
8. washThe combined organic layers were washed once with saturated NaCl
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customPurification by flash chromatography