Sodium Hydroxide → HCID 13389170, compound

HRID 2231487Notes

Reaction equation

HRID 2231487 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][CH2:19][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][CH2:19][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 14329998HCID 14329998, compound

Product 1

HCID 13389170HCID 13389170, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.94 g (0.0016 mole) of [4-acetyl-3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2-propylphenoxy]acetic acid ethyl ester in 50 ml of methanol and 8.2 ml (0.0082 mole) of 1.0N sodium hydroxide was stirred at reflux for 2 hours. Most of the solvent was removed in vacuo and the pH of the residue was adjusted to 2.0. The product was extracted with methylene chloride and the dried (magnesium sulfate) extract was concentrated in vacuo. The residue was crystallized from etherhexane to give 0.710 g (79% yield) of [4-acetyl-3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2-propylphenoxy]acetic acid, melting point 77°-80°.

Workup

  1. temperatureat reflux for 2 hours
  2. customMost of the solvent was removed in vacuo
  3. extractionThe product was extracted with methylene chloride
  4. dry with materialthe dried (magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo
  7. customThe residue was crystallized from etherhexane

Sources & evidence

ORD record
ord-97b38f32d06348258765e2aa5e2346f4
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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