Toluene → 4-[4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acid

HRID 2231497Notes

Reaction equation

HRID 2231497 reaction equation
C([O:3][C:4](=[O:47])[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][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[C:33]([OH:40])[C:32]=2[CH2:41][CH2:42][CH3:43])[C:10]=1[CH2:44][CH2:45][CH3:46])C.C1(C)C=CC=CC=1.C(OCC)(=O)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:47])=[O:3])=[C:10]([CH2:44][CH2:45][CH3:46])[C:11]=1[O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37](=[O:39])[CH3:38])=[C:33]([OH:40])[C:32]=1[CH2:41][CH2:42][CH3:43])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 143299904-[4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acid ethyl ester

Product 1

HCID 143299894-[4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.30 g of 4-[4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acid ethyl ester in 17 ml of 1.0N sodium hydroxide and 50 ml of methanol was stirred at reflux for 7 hours. The methanol was removed in vacuo and the residue was acidified. The product was extracted with ether and the dried (magnesium sulfate) extract was concentrated in vacuo to an oil (2.40 g). Chromatography on 150 g of silica gel and elution with a solvent mixture of 5% acetic acid: 70% toluene: 25% ethyl acetate gave 1.72 g (78% yield) of 4-[4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acid as a viscous oil.

Workup

  1. temperatureat reflux for 7 hours
  2. customThe methanol was removed in vacuo
  3. extractionThe product was extracted with ether
  4. dry with materialthe dried (magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo to an oil (2.40 g)
  7. washChromatography on 150 g of silica gel and elution
  8. additionwith a solvent mixture of 5% acetic acid

Sources & evidence

ORD record
ord-54776bf4de1849419ed955e22ccc1656
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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