Sodium Hydroxide → HCID 13389168, compound
Reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[C:25]([Cl:26])=[CH:24][C:23]([C:27](=[O:29])[CH3:28])=[C:22]([OH:30])[C:21]=2[CH2:31][CH2:32][CH3:33])[C:7]=1[CH2:34][CH2:35][CH3:36].[OH-].[Na+]>CO>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:37])=[O:2])=[C:7]([CH2:34][CH2:35][CH3:36])[C:8]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27](=[O:29])[CH3:28])=[C:22]([OH:30])[C:21]=1[CH2:31][CH2:32][CH3:33])(=[O:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.94 g (0.0036 mol) of [4-acetyl-3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester in 60 ml of methanol was added 60 ml of 1N sodium hydroxide (0.06 mol). The mixture was stirred at 25° for 20 hours. Most of the methanol was removed in vacuo and the aqueous solution was acidified to pH 4. The gummy precipitate was dissolved in ethyl acetate and washed with sodium chloride solution. The oil obtained on concentration of the ethyl acetate extract was purified by C18 reverse phase column chromatography, eluting with 60-80% methanol in water to yield a pale yellow oil which solidified. Recrystallization from cyclohexane-ether gave 790 mg, melting point 119°-121° (42% yield) of [4-acetyl-3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.