HCID 53945181, compound → [6-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid

HRID 2164922Notes

Reaction equation

HRID 2164922 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][CH:9]=[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])[C:7]=1[CH2:33][CH2:34][CH3:35]>CO.[OH-].[Na+]>[C:12]([C:11]1[C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH2:33][CH2:34][CH3:35])[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])=[CH:9][CH:10]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 1

HCID 53945181HCID 53945181, compound

Product 1

HCID 13389155[6-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.41 g of [6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester in 50 ml of methanol and 14 ml of 1N sodium hydroxide was stirred at reflux for 22 hours. The methanol was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The gummy product was extracted with ether and the crude extract was purified by chromatography on 60 g of silica gel. Elution with a solvent mixture of toluene:ethyl acetate:acetic acid (65:25:10) gave, after recrystallization from methylene chlorideether, 0.51 g (38%), mp 151°-155°, of [6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.

Workup

  1. temperatureat reflux for 22 hours
  2. customThe methanol was removed in vacuo
  3. extractionThe gummy product was extracted with ether
  4. extractionthe crude extract
  5. customwas purified by chromatography on 60 g of silica gel
  6. washElution
  7. additionwith a solvent mixture of toluene:ethyl acetate:acetic acid (65:25:10)
  8. customgave
  9. customafter recrystallization from methylene chlorideether, 0.51 g (38%), mp 151°-155°

Sources & evidence

ORD record
ord-1f03882bb4f44ea29f3f5050d2f6af59
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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