Potassium Hydroxide → 2-(Benzyloxy)-5-hydroxybenzoic acid

Reaction equation

CC1C=CC(S([O:11][C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])(=O)=O)=CC=1.[OH-].[K+]>C(O)C.O>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([CH:21]=1)[C:17]([OH:19])=[O:18]

Participants

Procedure

Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 37; 2.5 g, 6.06 mmol) was boiled with potassium hydroxide (2.38 g, 42.4 mmol) in a mixture of ethanol (60 ml) and water (15 ml) for 4 h. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (20 ml) and acidified with concentrated HCl. The mixture was extracted with ethyl acetate (3×30 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulphate and evaporated in vacuo to yield the title compound as a yellow oil. 1.35 g.