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 75; 9.0 g, 21.82 mmol) was boiled with potassium hydroxide (8.57 g, 153 mmol) in a mixture of ethanol (160 ml) and water (40 ml) for 3 h. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (250 ml), and then acidified with concentrated HCl. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over Na2SO4, and evaporated in vacuo to yield the title compound as a yellow oil. 5.2 g.