Sodium Hydroxide → HCID 13389167, compound

HRID 2164938Notes

Reaction equation

HRID 2164938 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]([Br: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(OCC)(=O)C>[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]([Br: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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14329993HCID 14329993, compound

Product 1

HCID 13389167HCID 13389167, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.1 g (0.0037 mol) of [4-acetyl-3-[3-(4-acetyl-6-bromo-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester in 50 ml of methanol was added 50 ml (0.05 mol) of 1N sodium hydroxide. The mixture was stirred at 25° for 16 hours and acidified to pH 4. The gummy precipitate was dissolved in ethyl acetate and washed with sodium choloride solution. The gummy solid obtained on concentration of the ethyl acetate was purified by C18 reverse phase column chromatography, eluting with 60% to 75% of methanol in water to yield 1.0 g, melting point 129°-130° (48% yield) of [4-acetyl-3-[3-(4-acetyl-6-bromo-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.

Workup

  1. washwashed with sodium choloride solution
  2. customThe gummy solid obtained on concentration of the ethyl acetate
  3. customwas purified by C18 reverse phase column chromatography
  4. washeluting with 60% to 75% of methanol in water

Sources & evidence

ORD record
ord-5aad7de7fb3744dea94ec68413a6ab8d
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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