Sodium Hydroxide → HCID 13389168, compound

HRID 2164941Notes

Reaction equation

HRID 2164941 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

HCID 14798Sodium HydroxideHCID 14329994HCID 14329994, compound

Product 1

HCID 13389168HCID 13389168, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customMost of the methanol was removed in vacuo
  2. dissolutionThe gummy precipitate was dissolved in ethyl acetate
  3. washwashed with sodium chloride solution
  4. customThe oil obtained on concentration of the ethyl acetate
  5. extractionextract
  6. customwas purified by C18 reverse phase column chromatography
  7. washeluting with 60-80% methanol in water
  8. customto yield a pale yellow oil which
  9. customRecrystallization from cyclohexane-ether

Sources & evidence

ORD record
ord-324dd8e4da544c9cba13865c12fd595b
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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