HCID 14329986, compound → HCID 13389166, compound

HRID 2164961Notes

Reaction equation

HRID 2164961 reaction equation
C([O:3][C:4](=[O:43])[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][O:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=2[CH2:37][CH2:38][CH3:39])[C:8]=1[CH2:40][CH2:41][CH3:42])C>CO.[OH-].[Na+]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:43])=[O:3])=[C:8]([CH2:40][CH2:41][CH3:42])[C:9]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[C:29]([OH:36])[C:28]=1[CH2:37][CH2:38][CH3:39])(=[O:15])[CH3:14]

Participants

4

Reactant 1

HCID 14329986HCID 14329986, compound

Product 1

HCID 13389166HCID 13389166, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.617 g (0.0044 mole) of [4-acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]acetic acid ethyl ester in 50 ml of methanol and 21.8 ml 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 ether-hexane to give 2.05 g (82% yield) of [4-acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]acetic acid, melting point 68°-71°.

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 ether-hexane

Sources & evidence

ORD record
ord-e140885b396c4609b738e28427681edf
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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