Sodium Hydroxide → 4-[4-Acetyl-3-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]butanoic acid

HRID 2231471Notes

Reaction equation

HRID 2231471 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([OH:34])[C:26]=2[CH2:35][CH2:36][CH3:37])[C:10]=1[CH2:38][CH2:39][CH3:40])C.[OH-].[Na+]>CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])=[C:10]([CH2:38][CH2:39][CH3:40])[C:11]=1[O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[C:27]([OH:34])[C:26]=1[CH2:35][CH2:36][CH3:37])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 143299774-[4-Acetyl-3-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]butanoic acid ethyl ester

Product 1

HCID 133891614-[4-Acetyl-3-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]butanoic acidYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.526 g (0.0009 mol) of 4-[4-acetyl-3-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]butanoic acid ethyl ester in 23 ml of methanol was added 23 ml (0.023 mol) of 1N sodium hydroxide. The mixture was stirred at 25° for 6 hours and the methanol was removed in vacuo. The aqueous solution was acidified to pH 3, the precipitate was dissolved in ethyl acetate and washed with sodium chloride solution. The oil obtained on concentration of the ethyl acetate was purified by column chromatography, eluting with 50% ethyl acetate-hexane and ethyl acetate to yield 0.4 g (80% yield) of 4-[4-acetyl-3-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]butanoic acid as a pale yellow oil which solidified (melting point 52°-58°).

Workup

  1. customthe methanol was removed in vacuo
  2. dissolutionthe precipitate was dissolved in ethyl acetate
  3. washwashed with sodium chloride solution
  4. customThe oil obtained on concentration of the ethyl acetate
  5. customwas purified by column chromatography
  6. washeluting with 50% ethyl acetate-hexane and ethyl acetate

Sources & evidence

ORD record
ord-87ecbd1d2a88492c934145d9a37cc637
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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