Sodium Hydroxide → HCID 14329996, compound

HRID 2231489Notes

Reaction equation

HRID 2231489 reaction equation
C([O:3][C:4](=[O:42])[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][CH2:21][CH2:22][CH2:23][O:24][C:25]2[C:30]([Cl:31])=[CH:29][C:28]([C:32](=[O:34])[CH3:33])=[C:27]([OH:35])[C:26]=2[CH2:36][CH2:37][CH3:38])[C:10]=1[CH2:39][CH2:40][CH3:41])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:42])=[O:3])=[C:10]([CH2:39][CH2:40][CH3:41])[C:11]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[C:30]([Cl:31])=[CH:29][C:28]([C:32](=[O:34])[CH3:33])=[C:27]([OH:35])[C:26]=1[CH2:36][CH2:37][CH3:38])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14329997HCID 14329997, compound

Product 1

HCID 14329996HCID 14329996, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.978 g (0.0016 mole) of 4-[4-acetyl -3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2-propylphenoxy]butanoic acid ethyl ester in 50 ml of methanol and 8.1 ml (0.0081 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 to give 0.850 g (91% of yield) of 4-[4-acetyl-3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2-propylphenoxy]butanoic acid as an oil.

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

Sources & evidence

ORD record
ord-2d97b3f1d0864a838a221943af4990f4
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

Loading…