Potassium Hydroxide → 3-(2,6dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12]C(=O)C1C=CC=CC=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A reaction vessel was charged with 3.75 g of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(benzyloxy)benzene, 5.0 g of 10% aqueous potassium hydroxide solution and 50 ml of methanol. After stirring at room temperature for 24 hours, the reaction mixture was concentrated. The concentrate was poured into water, and extracted twice with 150 m of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 2.56 g of 3-(2,6-dichloro-4-(benzyloxy)phenoxy)-1-propyl alcohol (90% yield).