Sodium Hydroxide → [4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid

HRID 2231479Notes

Reaction equation

HRID 2231479 reaction equation
C([O:3][C:4](=[O:45])[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][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O: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:8]=1[CH2:42][CH2:43][CH3:44])C.[OH-].[Na+]>CO>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:45])=[O:3])=[C:8]([CH2:42][CH2:43][CH3:44])[C:9]=1[O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O: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:15])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14329981[4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-ethoxy]-2-propylphenoxy]acetic acid ethyl ester

Product 1

HCID 14329980[4-Acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acidYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.25 g (0.002 mole) of [4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]-ethoxy]-2-propylphenoxy]acetic acid ethyl ester in 30 ml of methanol and 10 ml (0.01 mole) of 1.0N sodium hydroxide was stirred at reflux for 5 hours. Most of the solvent was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The product was extracted with methyl acetate and the dried (magnesium sulfate) extract was concentrated in vacuo to an oil which was purified by chromatography on 75 g of silica gel. Elution with toluene-ethyl acetate-acetic acid (65:25:10) gave 0.79 g (66% yield) of [4-acetyl-3-[2-[2-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid as an oil.

Workup

  1. temperatureat reflux for 5 hours
  2. customMost of the solvent was removed in vacuo
  3. extractionThe product was extracted with methyl acetate
  4. dry with materialthe dried (magnesium sulfate)
  5. extractionextract
  6. concentrationwas concentrated in vacuo to an oil which
  7. customwas purified by chromatography on 75 g of silica gel
  8. washElution with toluene-ethyl acetate-acetic acid (65:25:10)

Sources & evidence

ORD record
ord-75d87a2ad91e415eaab17f7408a13c3d
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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