Sodium Hydroxide → 4-Isopropoxy-3-(methoxymethyl)benzoic acid

Reaction equation

[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[CH2:15][O:16][CH3:17])([CH3:3])[CH3:2].[OH-].[Na+]>CCO.O>[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[CH2:15][O:16][CH3:17])([CH3:3])[CH3:2]

Participants

Procedure

A solution of methyl 4-isopropoxy-3-(methoxymethyl)benzoate (11.30 g; 47.42 mmol; 1 eq.) in EtOH (339 mL) at RT was treated with NaOH (47.42 mL; 5 M; 237.11 mmol; 5 eq.). The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated to give a yellow solid. It was taken up in water and the aqueous phase was washed with EtOAc and then acidified with HCl cc to pH 2. The aqueous layer was extracted with EtOAc (twice). The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a beige solid (9.71 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 12.39 (br s, 1H), 7.89-7.82 (m, 2H), 7.11-7.07 (d, J=8.75 Hz, 1H), 4.79-4.67 (sept, J=5.92 Hz, 1H), 4.39 (s, 2H), 3.35 (s, 3H), 1.31-1.28 (d, J=6.06 Hz, 6H). LC/MS (Method B): 223.2 (M−H)−. HPLC (Method A) Rt 3.71 min (Purity: 92.8%).