Sodium Hydroxide → [4-Acetyl-3-[2-[2-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]acetic acid

HRID 2164944Notes

Reaction equation

HRID 2164944 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:23]2[C:28]([Cl:29])=[CH:27][C:26]([C:30](=[O:32])[CH3:31])=[C:25]([OH:33])[C:24]=2[CH2:34][CH2:35][CH3:36])[C:8]=1[CH2:37][CH2:38][CH3:39])C.[OH-].[Na+]>CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:40])=[O:3])=[C:8]([CH2:37][CH2:38][CH3:39])[C:9]=1[O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:23]1[C:28]([Cl:29])=[CH:27][C:26]([C:30](=[O:32])[CH3:31])=[C:25]([OH:33])[C:24]=1[CH2:34][CH2:35][CH3:36])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14329995HCID 14329995, compound

Product 1

HCID 13389169[4-Acetyl-3-[2-[2-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]acetic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.400 g (0.00069 mol) of [4-acetyl-3-[2-[2-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]acetic acid ethyl ester in 15 ml of methanol was added 15 ml of 1N sodium hydroxide (0.015 mol). The mixture was stirred at 25° for 5 hours and the methanol was removed in vacuo. 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 was crystallized from cyclohexane to give 0.32 g, melting point 89°-91° (84% yield) of [4-acetyl-3-[2-[2-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-propylphenoxy]acetic acid.

Workup

  1. customthe 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. customwas crystallized from cyclohexane

Sources & evidence

ORD record
ord-d7a1f865efd7450aa8835b785250b734
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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