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

HRID 2231499Notes

Reaction equation

HRID 2231499 reaction equation
C([O:3][C:4](=[O:45])[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][O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([OH:38])[C:30]=2[CH2:39][CH2:40][CH3:41])[C:10]=1[CH2:42][CH2:43][CH3:44])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:45])=[O:3])=[C:10]([CH2:42][CH2:43][CH3:44])[C:11]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:37])[CH3:36])=[C:31]([OH:38])[C:30]=1[CH2:39][CH2:40][CH3:41])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 143299924-[4-Acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acid ethyl ester

Product 1

HCID 143299914-[4-Acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.71 g of 4-[4-acetyl-3-[4-[4-(4acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acid ethyl ester in 20 ml of 1.0N sodium hydroxide and 90 ml of methanol was stirred at reflux for 6.5 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. Chromatography on 150 g of silica gel and elution with a solvent mixture of 5% acetic acid: 70% toluene: 25% ethyl acetate gave 2.32 g (90% yield) of 4-[4-acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]butanoic acid as an oil.

Workup

  1. temperatureat reflux for 6.5 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
  7. washChromatography on 150 g of silica gel and elution
  8. additionwith a solvent mixture of 5% acetic acid

Sources & evidence

ORD record
ord-38f22043f60d437d9ef16a85c61562f4
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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