Sodium Hydroxide → HCID 13389162, compound

HRID 2231474Notes

Reaction equation

HRID 2231474 reaction equation
C([O:3][C:4](=[O:42])[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][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[C:28]([OH:35])[C:27]=2[CH2:36][CH2:37][CH3:38])[C:8]=1[CH2:39][CH2:40][CH3:41])C.[OH-].[Na+]>CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:42])=[O:3])=[C:8]([CH2:39][CH2:40][CH3:41])[C:9]=1[O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[C:28]([OH:35])[C:27]=1[CH2:36][CH2:37][CH3:38])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14329978HCID 14329978, compound

Product 1

HCID 13389162HCID 13389162, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.35 g (0.004 mole) of [4-acetyl-3-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid ethyl ester in 50 ml of methanol and 20 ml (0.02 mole) of 1.0N sodium hydroxide was stirred at reflux for 90 minutes. Most of the solvent was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N HCl. The gummy product was extracted with methylene chloride. The dried (magnesium sulfate) extract was concentrated in vacuo and the residue was crystallized from methylene chloride-hexane to give 2.06 g (92% yield) of [4-acetyl-3-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid, mp 74°-77°.

Workup

  1. temperatureat reflux for 90 minutes
  2. customMost of the solvent was removed in vacuo
  3. extractionThe gummy 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 methylene chloride-hexane

Sources & evidence

ORD record
ord-81d776a393cc4223a839f8f4e092bec4
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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