Hydrochloric Acid → 2-(3-Methyl-4-(propan-2-yl)phenoxy)acetic acid

Reaction equation

[CH:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12]C)=[O:11])=[CH:6][C:5]=1[CH3:16])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[CH:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][C:5]=1[CH3:16])([CH3:3])[CH3:2]

Participants

Procedure

A solution of methyl 2-(4-isopropyl-3-methylphenoxy)acetate (13.0 g, 58.5 mmol) in abs. ethanol (240 mL) was treated with aq. sodium hydroxide solution (13 mL, 5 M). The resulting solution was stirred for 4 h at ambient temperature, then poured into aq. HCl (800 mL, 1 N). This was extracted with ether (2×200 mL), and the extracts were washed with brine, combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the solid product, 2-(4-isopropyl-3-methylphenoxy)acetic acid, which was dried under vacuum (12.0 g, 58.5 mmol, 100%). 1H NMR (d6-DMSO, 300 MHz): δ 12.91 (1H, s), 7.12 (1H, d, J=8 Hz), 6.70-6.65 (2H, m), 4.58 (2H, s), 3.02 (1H, m, J=6.7 Hz), 2.24 (3H, s), 1.12 (6H, d, J=6.7 Hz).