Hydrochloric Acid → 2-(3-(2,6-Dimethylbenzyloxy)-4-methylphenyl)acetic acid

Reaction equation

[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]([O:16]CC)=[O:15])[CH:9]=[CH:10][C:11]=1[CH3:12].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]([OH:16])=[O:15])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

Procedure

To a stirred solution of Ethyl 2-(3-(2,6-dimethylbenzyloxy)-4-methylphenyl)acetate (Step D, 1.1 g, 3.5 mmol) in absolute ethanol (20 ml) was added 1N NaOH (7 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified to pH 3.5-4.0 by adding 1N HCl and concentrated. The residue was taken into chloroform and washed with 0.1N HCl, brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound.